4 N Broad Street

As we journey through downtown Brooksville, let’s make our way to 2 North Broad Street, where we’ll step into the bustling commercial history of the Jennings Building and the story of Maillis Grocery. Standing here, you’re at the heart of one of Brooksville’s most vibrant streets, a thoroughfare that has long been a lifeline for local commerce and community life.

The Jennings Building, which occupies this spot, has been a cornerstone of Brooksville’s downtown since the early 20th century. This structure was built in 1915 by James A. Jennings. He served as sheriff from 1885 to 1888, was the first president of the Hernando State Bank, and was Chairman of the County Commission. He was notably the cousin of William Sherman Jennings, a Brooksville resident, who served as the 18th Governor of Florida.

In 1914, the original Jennings Building (which had been owned by both Jennings and Chelf) and the other buildings on this block had been destroyed by fire. The fire was a particular threat at the turn of the 20th century since it quickly consumed dry timber homes and businesses. Firefighting depended entirely on the skill of the bucket brigade; at the turn of the 20th century, the City of Brooksville had no central water supply. The fire alarm at that time consisted of an old circular saw and a large mallet hung from a post on the Courthouse Square. 

Named after one of the town’s influential figures, James A. Jennings. This building was a hub of activity in its heyday. Over the years, it housed a variety of businesses that served the daily needs of Brooksville residents: a drug store where locals picked up remedies, a dentist’s office for those inevitable toothaches, a general store stocked with household essentials, a barbershop for a quick trim, a restaurant serving hearty meals, and even a pool hall where folks gathered for a bit of fun after a long day. Imagine the lively chatter of neighbors catching up, the clatter of pool cues, and the aroma of fresh-cooked food wafting through the air—this building was a microcosm of small-town life.

Among the many businesses that called the Jennings Building home, one stands out in the historical record: Maillis Grocery. While specific details about Maillis Grocery are scarce, research suggests it operated here during the early to mid-20th century, a time when small, family-run grocery stores were the lifeblood of communities like Brooksville. The Maillis family ran this store, providing essential goods to residents in an era before supermarkets dominated the landscape. Picture shelves stocked with canned goods, fresh produce from local farms, and barrels of flour and sugar, all carefully arranged to serve the needs of Brooksville’s growing population.

Located on Broad Street, one of the town’s main arteries, Maillis Grocery would have been a central gathering place for the community. In those days, a trip to the grocery store wasn’t just about shopping—it was a social event. Neighbors would linger to share news, children might beg for a piece of penny candy, and the store’s counter could double as a spot for impromptu town meetings. Maillis Grocery played a vital role in supporting local commerce, offering a convenient place for residents to buy what they needed without traveling far. It also contributed to the social fabric of Brooksville, fostering connections among neighbors in a town where everyone knew each other’s name.

The Jennings Building reflects the architectural style of early 20th-century commercial structures. The existing two-story brick masonry building retains much of its original architectural character and falls into the category of a “Mesker Storefront,” most commonly seen in the American Midwest. Observe the many cast-iron features like the original decorative cast-iron pilasters made by George L. Mesker & Company in Evansville, Indiana, surrounding the recessed entry storefronts along two sides of the building. Original prism glass windows (now replaced with clear glass) hung from the rosettes in the cast iron band. Coupled with a metal canopy above the storefront windows, this style allowed light to enter deep into the interior space while still providing shade. Note the cast-iron plate at the corner of Main and Broad. The flat parapet features simple corbelling, and windows are set singly and in pairs with concrete sills and simple corbelled brick hoods above. And take a peek at the “Rexall Store” floor tile from when Roy N. Chelf operated his drug store.

 It was a modest, functional building made of brick and wood, with large windows to display goods and invite passersby inside. Over the years, it may have seen small changes—perhaps a new coat of paint or an updated storefront—but its purpose remained the same: to serve the people of Brooksville. The building’s history mirrors the town’s evolution from its agricultural roots to a more diversified economy, with small businesses like Maillis Grocery playing a key role in that growth.

What’s fascinating about this stop is how it captures the spirit of a bygone era, when downtown Brooksville was a bustling hub of activity. The Jennings Building, with Maillis Grocery as one of its anchors, was part of a network of local businesses that kept the town thriving. Nearby, you had landmarks like the First National Bank at 1 North Main Street and the Presbyterian Church at 31 Broad Street, which itself was converted into a grocery store in 1947 by Henry Carlton Sr. These connections remind us that Broad Street was the commercial heart of Brooksville. In this place, the town’s economic and social life intertwine.

The structure has been repurposed over the years and turned into offices, commercial space, and restaurants. Its legacy lives on in the stories of Maillis Grocery and the Jennings Building. This spot reminds us of the vital role that small businesses played in shaping Brooksville’s identity, supporting its residents, and fostering a sense of community that still defines the town today.

"George Maillis, who had the grocery, probably, to me, might've been the most important man that ever lived in Brooksville. During the Depression, people had no money and they did trading. When he closed his stores the people owed him over millions of dollars. He never beefed the first time. Never made an issue." 

                                                                                                        - Bobby Snow

"George Maillis, who ran the store, was one of the finest people I ever knew. He carried a lot of people's credit that I don't think ever got paid for. But he'd always help people out. Back then they had four cinnamon rolls in a package and these hobos come through and George would always give them a pack of cinnamon rolls and a cold drink. Now, that might not have been the best food in the world, but it'd fill them up. I guess word got out among the hobos and a lot of them came through and George Maillis always gave them something."                                                                                          - Eddie McIntyre

As you stand here on Broad Street, take a moment to imagine the sights and sounds of Maillis Grocery in its prime. Picture a shopkeeper—perhaps Mr. or Mrs. Maillis—greeting customers by name, weighing out a pound of flour, or handing a child a piece of candy with a smile. This was where the people of Brooksville came together, not just to buy goods but to build a community. The Jennings Building and Maillis Grocery are a powerful reminder of the town’s enduring spirit.

Citations

Diane Bedard, “The Value of Restoring the Historic Jennings Building in Brooksville,” NatureCoaster.com, May 16, 2024, https://www.naturecoaster.com.

“4 N Broad Street — Tour BVL,” Tour BVL. Note: Exact dates for Maillis Grocery’s operation are not well-documented; the early to mid-20th century period is inferred based on oral histories and the building’s commercial peak. 

“4 N Broad Street — Tour BVL,” Tour BVL; Saundra Amrhein, “A Walking Tour Through Brooksville’s History,” Visit Florida, July 19, 2019, https://www.visitflorida.com. The social role of small groceries is a common theme in historical accounts of rural American towns. 

George Lansing Taylor Jr., “Jennings Building, Brooksville, FL,” (2010), George Lansing Taylor Collection Main Gallery, 2310, https://digitalcommons.unf.edu/historical_architecture_main/2310; Diane Bedard, "The Value of Restoring the Historic Jennings Building in Brooksville," NatureCoaster.com. 

“Tour of Historic Brooksville, Florida," Florida History, https://floridahistory.org; "4 N Broad Street — Tour BVL," Tour BVL. 

“These People They Are Brooksville,” Tampa Bay Times, “At the Forefront of Storefronts: Frank, Ben, and George Mesker” National Park Service website, “Hernando County the Sheriffs,” Old Brooksville in Photos and Stories, January 2008, Vol. 68

Welcome, folks, to a hidden gem of Brooksville’s past—Chelf’s Drug Store. We’re standing in the heart of downtown, where the pulse of this small town once beat strongest. It’s the early 20th century, and the air carries the faint scent of citrus from nearby groves, mingling with the sharper tang of medicinal tonics wafting out from this modest little shop. Picture a simple brick storefront, its large windows beckoning passersby with displays of colorful bottles and neatly stacked goods. This wasn’t just a place to pick up a prescription—it was a cornerstone of community life.

Step inside. The wooden floor creaks underfoot, and behind the counter stands the pharmacist—his white coat crisp as he measures out powders with a steady hand. Shelves groan under the weight of glass jars filled with remedies, from cough syrups to liniments, while a soda fountain in the corner hums with the promise of a cool treat. Kids clutch pennies, eyeing the candy jars, while their parents swap gossip about the latest goings-on—maybe the rum-runners stirring trouble up on Howell Avenue. In an era before big chain stores, Chelf’s was where Brooksville came for healing, comfort, and connection.

We don’t have a scrapbook full of details about Chelf’s—its story hasn’t made it into the big history books or online archives like some of its flashier neighbors. But that’s what makes it special. It’s one of those quiet, everyday places that kept this town ticking. Research suggests it thrived in the early to mid-20th century, a time when Brooksville was growing from its plantation roots into a bustling hub of planters, growers, and cattlemen. Pharmacies like this one were lifelines, stitching together a community where folks knew each other by name.

Look around—this spot, whatever it’s become today, was part of a downtown alive with small businesses. Just a stone’s throw away on Broad Street, you would find the place buzzing with barbers and grocers, or the Presbyterian Church turned grocery by ’47. Chelf’s Drug Store fit right into that tapestry, offering cures for ailments and a place to linger when the days got long. Its walls soaked up tales of hard times and good, from the boom of the citrus trade to the lean years of the Depression.

Now, here’s the twist: Chelf’s is a bit of a ghost in the records. No grand plaques or tourist brochures sing its praises, which might mean it was a family-run outfit, too small to catch the historian’s eye. But that mystery only adds to its charm. As you stand here, imagine the clink of a glass bottle, the rustle of a paper bag, and the chatter of neighbors. Look down at the penny tiles that still remain underfoot, paying homage to Roy Chelf and his Rexall Drug Store. This wasn’t just a business—it was part of Brooksville’s heartbeat, one prescription at a time.

Citations

Saundra Amrhein, "A Walking Tour Through Brooksville’s History," Visit Florida, July 19, 2019, https://www.visitflorida.com. Note: Specific details about Chelf’s Drug Store are unavailable; the description is inferred from the typical role of small-town pharmacies in the early 20th century. 

“Tour of Historic Brooksville, Florida,” Florida History, https://floridahistory.org. The timeframe and community role are contextualized based on Brooksville’s commercial growth during this period. 

“4 N Broad Street — Tour BVL,” Tour BVL, https://www.tourbvl.com. The Jennings Building and Presbyterian Church examples provide a comparative backdrop.

2/4 North Broad Street – Maillis Grocery (The Jennings Building)

As we journey through downtown Brooksville, let’s make our way to 2 North Broad Street, where we’ll step into the bustling commercial history of the Jennings Building and the story of Maillis Grocery. Standing here, you’re at the heart of one of Brooksville’s most vibrant streets, a thoroughfare that has long been a lifeline for local commerce and community life.

The Jennings Building, which occupies this spot, has been a cornerstone of Brooksville’s downtown since the early 20th century. This structure was built in 1915 by James A. Jennings. He served as sheriff from 1885 to 1888, was the first president of the Hernando State Bank, and was Chairman of the County Commission. He was notably the cousin of William Sherman Jennings, a Brooksville resident, who served as the 18th Governor of Florida.

In 1914, the original Jennings Building (which had been owned by both Jennings and Chelf) and the other buildings on this block had been destroyed by fire. The fire was a particular threat at the turn of the 20th century since it quickly consumed dry timber homes and businesses. Firefighting depended entirely on the skill of the bucket brigade; at the turn of the 20th century, the City of Brooksville had no central water supply. The fire alarm at that time consisted of an old circular saw and a large mallet hung from a post on the Courthouse Square. 

Named after one of the town’s influential figures, James A. Jennings. This building was a hub of activity in its heyday. Over the years, it housed a variety of businesses that served the daily needs of Brooksville residents: a drug store where locals picked up remedies, a dentist’s office for those inevitable toothaches, a general store stocked with household essentials, a barbershop for a quick trim, a restaurant serving hearty meals, and even a pool hall where folks gathered for a bit of fun after a long day. Imagine the lively chatter of neighbors catching up, the clatter of pool cues, and the aroma of fresh-cooked food wafting through the air—this building was a microcosm of small-town life.

Among the many businesses that called the Jennings Building home, one stands out in the historical record: Maillis Grocery. While specific details about Maillis Grocery are scarce, research suggests it operated here during the early to mid-20th century, a time when small, family-run grocery stores were the lifeblood of communities like Brooksville. The Maillis family ran this store, providing essential goods to residents in an era before supermarkets dominated the landscape. Picture shelves stocked with canned goods, fresh produce from local farms, and barrels of flour and sugar, all carefully arranged to serve the needs of Brooksville’s growing population.

Located on Broad Street, one of the town’s main arteries, Maillis Grocery would have been a central gathering place for the community. In those days, a trip to the grocery store wasn’t just about shopping—it was a social event. Neighbors would linger to share news, children might beg for a piece of penny candy, and the store’s counter could double as a spot for impromptu town meetings. Maillis Grocery played a vital role in supporting local commerce, offering a convenient place for residents to buy what they needed without traveling far. It also contributed to the social fabric of Brooksville, fostering connections among neighbors in a town where everyone knew each other’s name.

The Jennings Building reflects the architectural style of early 20th-century commercial structures. The existing two-story brick masonry building retains much of its original architectural character and falls into the category of a “Mesker Storefront,” most commonly seen in the American Midwest. Observe the many cast-iron features like the original decorative cast-iron pilasters made by George L. Mesker & Company in Evansville, Indiana, surrounding the recessed entry storefronts along two sides of the building. Original prism glass windows (now replaced with clear glass) hung from the rosettes in the cast iron band. Coupled with a metal canopy above the storefront windows, this style allowed light to enter deep into the interior space while still providing shade. Note the cast-iron plate at the corner of Main and Broad. The flat parapet features simple corbelling, and windows are set singly and in pairs with concrete sills and simple corbelled brick hoods above. And take a peek at the “Rexall Store” floor tile from when Roy N. Chelf operated his drug store.

 It was a modest, functional building made of brick and wood, with large windows to display goods and invite passersby inside. Over the years, it may have seen small changes—perhaps a new coat of paint or an updated storefront—but its purpose remained the same: to serve the people of Brooksville. The building’s history mirrors the town’s evolution from its agricultural roots to a more diversified economy, with small businesses like Maillis Grocery playing a key role in that growth.

What’s fascinating about this stop is how it captures the spirit of a bygone era, when downtown Brooksville was a bustling hub of activity. The Jennings Building, with Maillis Grocery as one of its anchors, was part of a network of local businesses that kept the town thriving. Nearby, you had landmarks like the First National Bank at 1 North Main Street and the Presbyterian Church at 31 Broad Street, which itself was converted into a grocery store in 1947 by Henry Carlton Sr. These connections remind us that Broad Street was the commercial heart of Brooksville. In this place, the town’s economic and social life intertwine.

The structure has been repurposed over the years and turned into offices, commercial space, and restaurants. Its legacy lives on in the stories of Maillis Grocery and the Jennings Building. This spot reminds us of the vital role that small businesses played in shaping Brooksville’s identity, supporting its residents, and fostering a sense of community that still defines the town today.

"George Maillis, who had the grocery, probably, to me, might've been the most important man that ever lived in Brooksville. During the Depression, people had no money and they did trading. When he closed his stores the people owed him over millions of dollars. He never beefed the first time. Never made an issue." 

                                                                                                        - Bobby Snow

"George Maillis, who ran the store, was one of the finest people I ever knew. He carried a lot of people's credit that I don't think ever got paid for. But he'd always help people out. Back then they had four cinnamon rolls in a package and these hobos come through and George would always give them a pack of cinnamon rolls and a cold drink. Now, that might not have been the best food in the world, but it'd fill them up. I guess word got out among the hobos and a lot of them came through and George Maillis always gave them something."                                                                                          - Eddie McIntyre

As you stand here on Broad Street, take a moment to imagine the sights and sounds of Maillis Grocery in its prime. Picture a shopkeeper—perhaps Mr. or Mrs. Maillis—greeting customers by name, weighing out a pound of flour, or handing a child a piece of candy with a smile. This was where the people of Brooksville came together, not just to buy goods but to build a community. The Jennings Building and Maillis Grocery are a powerful reminder of the town’s enduring spirit.

Citations

Diane Bedard, “The Value of Restoring the Historic Jennings Building in Brooksville,” NatureCoaster.com, May 16, 2024, https://www.naturecoaster.com.

“4 N Broad Street — Tour BVL,” Tour BVL. Note: Exact dates for Maillis Grocery’s operation are not well-documented; the early to mid-20th century period is inferred based on oral histories and the building’s commercial peak. 

“4 N Broad Street — Tour BVL,” Tour BVL; Saundra Amrhein, “A Walking Tour Through Brooksville’s History,” Visit Florida, July 19, 2019, https://www.visitflorida.com. The social role of small groceries is a common theme in historical accounts of rural American towns. 

George Lansing Taylor Jr., “Jennings Building, Brooksville, FL,” (2010), George Lansing Taylor Collection Main Gallery, 2310, https://digitalcommons.unf.edu/historical_architecture_main/2310; Diane Bedard, "The Value of Restoring the Historic Jennings Building in Brooksville," NatureCoaster.com. 

“Tour of Historic Brooksville, Florida," Florida History, https://floridahistory.org; "4 N Broad Street — Tour BVL," Tour BVL. 

“These People They Are Brooksville,” Tampa Bay Times, “At the Forefront of Storefronts: Frank, Ben, and George Mesker” National Park Service website, “Hernando County the Sheriffs,” Old Brooksville in Photos and Stories, January 2008, Vol. 68

As we journey through downtown Brooksville, let’s make our way to 2 North Broad Street, where we’ll step into the bustling commercial history of the Jennings Building and the story of Maillis Grocery. Standing here, you’re at the heart of one of Brooksville’s most vibrant streets, a thoroughfare that has long been a lifeline for local commerce and community life.

The Jennings Building, which occupies this spot, has been a cornerstone of Brooksville’s downtown since the early 20th century. This structure was built in 1915 by James A. Jennings. He served as sheriff from 1885 to 1888, was the first president of the Hernando State Bank, and was Chairman of the County Commission. He was notably the cousin of William Sherman Jennings, a Brooksville resident, who served as the 18th Governor of Florida.

In 1914, the original Jennings Building (which had been owned by both Jennings and Chelf) and the other buildings on this block had been destroyed by fire. The fire was a particular threat at the turn of the 20th century since it quickly consumed dry timber homes and businesses. Firefighting depended entirely on the skill of the bucket brigade; at the turn of the 20th century, the City of Brooksville had no central water supply. The fire alarm at that time consisted of an old circular saw and a large mallet hung from a post on the Courthouse Square. 

Named after one of the town’s influential figures, James A. Jennings. This building was a hub of activity in its heyday. Over the years, it housed a variety of businesses that served the daily needs of Brooksville residents: a drug store where locals picked up remedies, a dentist’s office for those inevitable toothaches, a general store stocked with household essentials, a barbershop for a quick trim, a restaurant serving hearty meals, and even a pool hall where folks gathered for a bit of fun after a long day. Imagine the lively chatter of neighbors catching up, the clatter of pool cues, and the aroma of fresh-cooked food wafting through the air—this building was a microcosm of small-town life.

Among the many businesses that called the Jennings Building home, one stands out in the historical record: Maillis Grocery. While specific details about Maillis Grocery are scarce, research suggests it operated here during the early to mid-20th century, a time when small, family-run grocery stores were the lifeblood of communities like Brooksville. The Maillis family ran this store, providing essential goods to residents in an era before supermarkets dominated the landscape. Picture shelves stocked with canned goods, fresh produce from local farms, and barrels of flour and sugar, all carefully arranged to serve the needs of Brooksville’s growing population.

Located on Broad Street, one of the town’s main arteries, Maillis Grocery would have been a central gathering place for the community. In those days, a trip to the grocery store wasn’t just about shopping—it was a social event. Neighbors would linger to share news, children might beg for a piece of penny candy, and the store’s counter could double as a spot for impromptu town meetings. Maillis Grocery played a vital role in supporting local commerce, offering a convenient place for residents to buy what they needed without traveling far. It also contributed to the social fabric of Brooksville, fostering connections among neighbors in a town where everyone knew each other’s name.

The Jennings Building reflects the architectural style of early 20th-century commercial structures. The existing two-story brick masonry building retains much of its original architectural character and falls into the category of a “Mesker Storefront,” most commonly seen in the American Midwest. Observe the many cast-iron features like the original decorative cast-iron pilasters made by George L. Mesker & Company in Evansville, Indiana, surrounding the recessed entry storefronts along two sides of the building. Original prism glass windows (now replaced with clear glass) hung from the rosettes in the cast iron band. Coupled with a metal canopy above the storefront windows, this style allowed light to enter deep into the interior space while still providing shade. Note the cast-iron plate at the corner of Main and Broad. The flat parapet features simple corbelling, and windows are set singly and in pairs with concrete sills and simple corbelled brick hoods above. And take a peek at the “Rexall Store” floor tile from when Roy N. Chelf operated his drug store.

 It was a modest, functional building made of brick and wood, with large windows to display goods and invite passersby inside. Over the years, it may have seen small changes—perhaps a new coat of paint or an updated storefront—but its purpose remained the same: to serve the people of Brooksville. The building’s history mirrors the town’s evolution from its agricultural roots to a more diversified economy, with small businesses like Maillis Grocery playing a key role in that growth.

What’s fascinating about this stop is how it captures the spirit of a bygone era, when downtown Brooksville was a bustling hub of activity. The Jennings Building, with Maillis Grocery as one of its anchors, was part of a network of local businesses that kept the town thriving. Nearby, you had landmarks like the First National Bank at 1 North Main Street and the Presbyterian Church at 31 Broad Street, which itself was converted into a grocery store in 1947 by Henry Carlton Sr. These connections remind us that Broad Street was the commercial heart of Brooksville. In this place, the town’s economic and social life intertwine.

The structure has been repurposed over the years and turned into offices, commercial space, and restaurants. Its legacy lives on in the stories of Maillis Grocery and the Jennings Building. This spot reminds us of the vital role that small businesses played in shaping Brooksville’s identity, supporting its residents, and fostering a sense of community that still defines the town today.

"George Maillis, who had the grocery, probably, to me, might've been the most important man that ever lived in Brooksville. During the Depression, people had no money and they did trading. When he closed his stores the people owed him over millions of dollars. He never beefed the first time. Never made an issue." 

                                                                                                        - Bobby Snow

"George Maillis, who ran the store, was one of the finest people I ever knew. He carried a lot of people's credit that I don't think ever got paid for. But he'd always help people out. Back then they had four cinnamon rolls in a package and these hobos come through and George would always give them a pack of cinnamon rolls and a cold drink. Now, that might not have been the best food in the world, but it'd fill them up. I guess word got out among the hobos and a lot of them came through and George Maillis always gave them something."                                                                                          - Eddie McIntyre

As you stand here on Broad Street, take a moment to imagine the sights and sounds of Maillis Grocery in its prime. Picture a shopkeeper—perhaps Mr. or Mrs. Maillis—greeting customers by name, weighing out a pound of flour, or handing a child a piece of candy with a smile. This was where the people of Brooksville came together, not just to buy goods but to build a community. The Jennings Building and Maillis Grocery are a powerful reminder of the town’s enduring spirit.

Citations

Diane Bedard, “The Value of Restoring the Historic Jennings Building in Brooksville,” NatureCoaster.com, May 16, 2024, https://www.naturecoaster.com.

“4 N Broad Street — Tour BVL,” Tour BVL. Note: Exact dates for Maillis Grocery’s operation are not well-documented; the early to mid-20th century period is inferred based on oral histories and the building’s commercial peak. 

“4 N Broad Street — Tour BVL,” Tour BVL; Saundra Amrhein, “A Walking Tour Through Brooksville’s History,” Visit Florida, July 19, 2019, https://www.visitflorida.com. The social role of small groceries is a common theme in historical accounts of rural American towns. 

George Lansing Taylor Jr., “Jennings Building, Brooksville, FL,” (2010), George Lansing Taylor Collection Main Gallery, 2310, https://digitalcommons.unf.edu/historical_architecture_main/2310; Diane Bedard, "The Value of Restoring the Historic Jennings Building in Brooksville," NatureCoaster.com. 

“Tour of Historic Brooksville, Florida," Florida History, https://floridahistory.org; "4 N Broad Street — Tour BVL," Tour BVL. 

“These People They Are Brooksville,” Tampa Bay Times, “At the Forefront of Storefronts: Frank, Ben, and George Mesker” National Park Service website, “Hernando County the Sheriffs,” Old Brooksville in Photos and Stories, January 2008, Vol. 68

Welcome, folks, to a hidden gem of Brooksville’s past—Chelf’s Drug Store. We’re standing in the heart of downtown, where the pulse of this small town once beat strongest. It’s the early 20th century, and the air carries the faint scent of citrus from nearby groves, mingling with the sharper tang of medicinal tonics wafting out from this modest little shop. Picture a simple brick storefront, its large windows beckoning passersby with displays of colorful bottles and neatly stacked goods. This wasn’t just a place to pick up a prescription—it was a cornerstone of community life.

Step inside. The wooden floor creaks underfoot, and behind the counter stands the pharmacist—his white coat crisp as he measures out powders with a steady hand. Shelves groan under the weight of glass jars filled with remedies, from cough syrups to liniments, while a soda fountain in the corner hums with the promise of a cool treat. Kids clutch pennies, eyeing the candy jars, while their parents swap gossip about the latest goings-on—maybe the rum-runners stirring trouble up on Howell Avenue. In an era before big chain stores, Chelf’s was where Brooksville came for healing, comfort, and connection.

We don’t have a scrapbook full of details about Chelf’s—its story hasn’t made it into the big history books or online archives like some of its flashier neighbors. But that’s what makes it special. It’s one of those quiet, everyday places that kept this town ticking. Research suggests it thrived in the early to mid-20th century, a time when Brooksville was growing from its plantation roots into a bustling hub of planters, growers, and cattlemen. Pharmacies like this one were lifelines, stitching together a community where folks knew each other by name.

Look around—this spot, whatever it’s become today, was part of a downtown alive with small businesses. Just a stone’s throw away on Broad Street, you would find the place buzzing with barbers and grocers, or the Presbyterian Church turned grocery by ’47. Chelf’s Drug Store fit right into that tapestry, offering cures for ailments and a place to linger when the days got long. Its walls soaked up tales of hard times and good, from the boom of the citrus trade to the lean years of the Depression.

Now, here’s the twist: Chelf’s is a bit of a ghost in the records. No grand plaques or tourist brochures sing its praises, which might mean it was a family-run outfit, too small to catch the historian’s eye. But that mystery only adds to its charm. As you stand here, imagine the clink of a glass bottle, the rustle of a paper bag, and the chatter of neighbors. Look down at the penny tiles that still remain underfoot, paying homage to Roy Chelf and his Rexall Drug Store. This wasn’t just a business—it was part of Brooksville’s heartbeat, one prescription at a time.

Citations

Saundra Amrhein, "A Walking Tour Through Brooksville’s History," Visit Florida, July 19, 2019, https://www.visitflorida.com. Note: Specific details about Chelf’s Drug Store are unavailable; the description is inferred from the typical role of small-town pharmacies in the early 20th century. 

“Tour of Historic Brooksville, Florida,” Florida History, https://floridahistory.org. The timeframe and community role are contextualized based on Brooksville’s commercial growth during this period. 

“4 N Broad Street — Tour BVL,” Tour BVL, https://www.tourbvl.com. The Jennings Building and Presbyterian Church examples provide a comparative backdrop.

As we journey through downtown Brooksville, let’s make our way to 2 North Broad Street, where we’ll step into the bustling commercial history of the Jennings Building and the story of Maillis Grocery. Standing here, you’re at the heart of one of Brooksville’s most vibrant streets, a thoroughfare that has long been a lifeline for local commerce and community life.

The Jennings Building, which occupies this spot, has been a cornerstone of Brooksville’s downtown since the early 20th century. This structure was built in 1915 by James A. Jennings. He served as sheriff from 1885 to 1888, was the first president of the Hernando State Bank, and was Chairman of the County Commission. He was notably the cousin of William Sherman Jennings, a Brooksville resident, who served as the 18th Governor of Florida.

In 1914, the original Jennings Building (which had been owned by both Jennings and Chelf) and the other buildings on this block had been destroyed by fire. The fire was a particular threat at the turn of the 20th century since it quickly consumed dry timber homes and businesses. Firefighting depended entirely on the skill of the bucket brigade; at the turn of the 20th century, the City of Brooksville had no central water supply. The fire alarm at that time consisted of an old circular saw and a large mallet hung from a post on the Courthouse Square. 

Named after one of the town’s influential figures, James A. Jennings. This building was a hub of activity in its heyday. Over the years, it housed a variety of businesses that served the daily needs of Brooksville residents: a drug store where locals picked up remedies, a dentist’s office for those inevitable toothaches, a general store stocked with household essentials, a barbershop for a quick trim, a restaurant serving hearty meals, and even a pool hall where folks gathered for a bit of fun after a long day. Imagine the lively chatter of neighbors catching up, the clatter of pool cues, and the aroma of fresh-cooked food wafting through the air—this building was a microcosm of small-town life.

Among the many businesses that called the Jennings Building home, one stands out in the historical record: Maillis Grocery. While specific details about Maillis Grocery are scarce, research suggests it operated here during the early to mid-20th century, a time when small, family-run grocery stores were the lifeblood of communities like Brooksville. The Maillis family ran this store, providing essential goods to residents in an era before supermarkets dominated the landscape. Picture shelves stocked with canned goods, fresh produce from local farms, and barrels of flour and sugar, all carefully arranged to serve the needs of Brooksville’s growing population.

Located on Broad Street, one of the town’s main arteries, Maillis Grocery would have been a central gathering place for the community. In those days, a trip to the grocery store wasn’t just about shopping—it was a social event. Neighbors would linger to share news, children might beg for a piece of penny candy, and the store’s counter could double as a spot for impromptu town meetings. Maillis Grocery played a vital role in supporting local commerce, offering a convenient place for residents to buy what they needed without traveling far. It also contributed to the social fabric of Brooksville, fostering connections among neighbors in a town where everyone knew each other’s name.

The Jennings Building reflects the architectural style of early 20th-century commercial structures. The existing two-story brick masonry building retains much of its original architectural character and falls into the category of a “Mesker Storefront,” most commonly seen in the American Midwest. Observe the many cast-iron features like the original decorative cast-iron pilasters made by George L. Mesker & Company in Evansville, Indiana, surrounding the recessed entry storefronts along two sides of the building. Original prism glass windows (now replaced with clear glass) hung from the rosettes in the cast iron band. Coupled with a metal canopy above the storefront windows, this style allowed light to enter deep into the interior space while still providing shade. Note the cast-iron plate at the corner of Main and Broad. The flat parapet features simple corbelling, and windows are set singly and in pairs with concrete sills and simple corbelled brick hoods above. And take a peek at the “Rexall Store” floor tile from when Roy N. Chelf operated his drug store.

 It was a modest, functional building made of brick and wood, with large windows to display goods and invite passersby inside. Over the years, it may have seen small changes—perhaps a new coat of paint or an updated storefront—but its purpose remained the same: to serve the people of Brooksville. The building’s history mirrors the town’s evolution from its agricultural roots to a more diversified economy, with small businesses like Maillis Grocery playing a key role in that growth.

What’s fascinating about this stop is how it captures the spirit of a bygone era, when downtown Brooksville was a bustling hub of activity. The Jennings Building, with Maillis Grocery as one of its anchors, was part of a network of local businesses that kept the town thriving. Nearby, you had landmarks like the First National Bank at 1 North Main Street and the Presbyterian Church at 31 Broad Street, which itself was converted into a grocery store in 1947 by Henry Carlton Sr. These connections remind us that Broad Street was the commercial heart of Brooksville. In this place, the town’s economic and social life intertwine.

The structure has been repurposed over the years and turned into offices, commercial space, and restaurants. Its legacy lives on in the stories of Maillis Grocery and the Jennings Building. This spot reminds us of the vital role that small businesses played in shaping Brooksville’s identity, supporting its residents, and fostering a sense of community that still defines the town today.

"George Maillis, who had the grocery, probably, to me, might've been the most important man that ever lived in Brooksville. During the Depression, people had no money and they did trading. When he closed his stores the people owed him over millions of dollars. He never beefed the first time. Never made an issue." 

                                                                                                        - Bobby Snow

"George Maillis, who ran the store, was one of the finest people I ever knew. He carried a lot of people's credit that I don't think ever got paid for. But he'd always help people out. Back then they had four cinnamon rolls in a package and these hobos come through and George would always give them a pack of cinnamon rolls and a cold drink. Now, that might not have been the best food in the world, but it'd fill them up. I guess word got out among the hobos and a lot of them came through and George Maillis always gave them something."                                                                                          - Eddie McIntyre

As you stand here on Broad Street, take a moment to imagine the sights and sounds of Maillis Grocery in its prime. Picture a shopkeeper—perhaps Mr. or Mrs. Maillis—greeting customers by name, weighing out a pound of flour, or handing a child a piece of candy with a smile. This was where the people of Brooksville came together, not just to buy goods but to build a community. The Jennings Building and Maillis Grocery are a powerful reminder of the town’s enduring spirit.

Citations

Diane Bedard, “The Value of Restoring the Historic Jennings Building in Brooksville,” NatureCoaster.com, May 16, 2024, https://www.naturecoaster.com.

“4 N Broad Street — Tour BVL,” Tour BVL. Note: Exact dates for Maillis Grocery’s operation are not well-documented; the early to mid-20th century period is inferred based on oral histories and the building’s commercial peak. 

“4 N Broad Street — Tour BVL,” Tour BVL; Saundra Amrhein, “A Walking Tour Through Brooksville’s History,” Visit Florida, July 19, 2019, https://www.visitflorida.com. The social role of small groceries is a common theme in historical accounts of rural American towns. 

George Lansing Taylor Jr., “Jennings Building, Brooksville, FL,” (2010), George Lansing Taylor Collection Main Gallery, 2310, https://digitalcommons.unf.edu/historical_architecture_main/2310; Diane Bedard, "The Value of Restoring the Historic Jennings Building in Brooksville," NatureCoaster.com. 

“Tour of Historic Brooksville, Florida," Florida History, https://floridahistory.org; "4 N Broad Street — Tour BVL," Tour BVL. 

“These People They Are Brooksville,” Tampa Bay Times, “At the Forefront of Storefronts: Frank, Ben, and George Mesker” National Park Service website, “Hernando County the Sheriffs,” Old Brooksville in Photos and Stories, January 2008, Vol. 68