Tallahassee: Florida’s Up-and-Coming Cool City

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Color me biased, but I think Florida gets such an undue bad rap these days. When I was a kid growing up outside Jacksonville, my home state was known for its beaches, great college football, awesome Cuban food (and Mexican food, and seafood in general), and retirees. But by the time I was attending Florida State University it had undergone a terrible rebranding to the state of apocalyptic weather, pythons devouring alligators and then exploding, bath salts-induced cannibalism, @FloridaMan, and retirees.

Haters gonna hate, but I love the Sunshine State. Miami is among the best American cities for beaches and nightlife, and St. Petersburg has transformed into a millennial yuppie capital on par with Austin or Portland. And now another incredibly unlikely suspect is adding its name to the list of Florida cities that all the cool kids my age want to be in.

The boring, bureaucratic state capital that was once a Southern Georgian cultural castoff with a pathetic facade of urbanness is now growing and changing faster than any city I’ve ever seen. This week as I visit some old college friends, I’m loving what I’m seeing in Tallahassee.

tallahassee up and coming construction

Tallahassee: an abbreviated and uneventful history

The first time I went to Tallahassee I was 17 years old, going for a campus visit before I started my final year of high school and began applying to universities. Coming from a town of 9,000 where we lived on a dirt road and “no shoes, no shirt, no problem” was the general rule in the local grocery store, I fell in love with Tallahassee immediately.

The city proper only had a population of around 175,000 people, but I had zero frame of reference for what a number like that meant. All I saw was the four-block ‘downtown’ area where the occasional cafe or restaurant was squeezed between the Florida Organization of Counties and the Leon County Clerk of Courts, under the shadow of obnoxiously tall Hotel Duval and the complementary state-erected phallus of the Capitol Building. I had hit the ‘big city’.

But, lolol, nope. After my first year of living the dorm life and now and then trepedatiously venturing a block or two off of the university campus to the bars on Pensacola street where dirty-looking men in their mid-thirties saw to it that the eighteen-year-old freshman girls never wanted for a drink, I was over it.

Way back then (from 2009 to 2013), Tallahassee was kind of meh. I didn’t hate it as much as most other third- and fourth-year students came to before escaping, but there wasn’t a whole lot to love either.

Some gross clubs that kept getting shut down for e. coli and mold infestations, the old man who cycled nude up and down Apalachee Parkway, the dystopically deserted Tallahassee Mall where you could always faintly hear the giggling spirits of dead children from every horror movie ever, and the super expensive bars and restaurants in Midtown where Tally’s 17 young professionals lived: that was all enough to keep you from dying for four years, but beyond that there wasn’t much going on.

tallahassee up and coming food trucks

There are food trucks now? wut

Which is why, when I visited Tallahassee for the first time in over a year last month, I couldn’t shut up about how cool everything had gotten so fast.

Tallahassee’s urban development

Something magical started happening in Florida’s capital about two years ago (suspiciously shortly after I left…). Money that had been held up through the financial crisis started flowing again. Big name developers moved in. Florida State University shook things up a bit, tuition rates went up, and suddenly ten billion South Florida trust fund kids were enrolling as freshmen. I’m not sure what the cause is, but the effect has been clear.

tallahassee up and coming signs

And these tourist sign thingies? Where are these coming from??

Neighborhoods that I was warned against walking around by myself at night as a freshman have swapped ominous barbed wire fences for food trucks and breweries. Student apartments are cropping up in big city-style developments with trendy shops and cafes on the ground floor and swanky apartments with obnoxious views of the stadium above. There’s even a burgeoning startup community silently creeping in and building up.

What the fuck is going on in Tallahassee?

It’s not that it’s ever been such an awful place to spend a few years. For a college student, I always thought it was fine. But on your 23rd birthday, if you look around and find yourself still in Tallahassee, in my day, it provoked an early onset mid-life crisis. It’s always been a town that had enough trashy bars to keep the students distracted and passing their STDs back and forth while the grownups hid in the safety of their Midtown townhouses and drowned their semi-urban misery by drinking more than the students ten minutes to the south did.

But now it’s like Tallahassee is looking at its bigger siblings like Miami and St. Petersburg with envy. It wants to earn the adoration of young professionals and passers-through just like its shinier southern neighbors. So it’s getting a perm, slipping into some spandex pants and stilettos, and lighting up a cigarette.

Tallahassee travel highlights

Back when I did live in Tallahassee, I was hosting Couchsurfers once or twice a month, and I got mixed reviews on my college town back then. Most people stopped there because there’s really nothing else within a four or five hour radius of the state capital, and it makes a logical overnight point between places like New Orleans and South Florida.

Nowadays I’d recommend it even more for that stopping point, but whereas in 2010 I’d have discouraged you from spending more than a day or two, I’m changing my tune now. I think you should spend a short week in Tally as part of any trip through Florida or the Gulf Coast. And here are just a few of the highlights you could hit in that week:

Railroad Square

The neighborhood south of FSU campus and north of FAMU was just a really weird wtf of a place when I lived in Tallahassee. Part hipster, part ghetto, part nebulous nothing neighborhood between the universities. Now it’s sort of the same, but just more so and way better?

Railroad Square Art Park is the traditional heart and soul of the Railroad Square neighborhood and Tallahassee’s hipster and artistic communities. The first Friday of every month is First Friday at Railroad Square, where all the local art and craft vendors open at night, showcasing their galleries and works for sale, sometimes with refreshments and hors d’oeuvres. From 6 to 9 pm every First Friday, students, artists, and families from around Tallahassee converge here and bridge their demographic gaps for several hours of peaceful coexistence.

Railroad Square Art Park. Photo by Ryan Hovatter via Wikimedia Commons.

All Saints Cafe has been there since my undergrad days, where it’s always been an ideal spot for coffee, vegan baked goods, studying, and beard-watching. I still think of it as the heart of the Railroad Square neighborhood, but the true center seems to have shifted just a tad west toward the university.

Tallahassee up and coming warehouse

The Warehouse, another one of my undergrad favorites, is, basically, a warehouse. There’s a few pool tables and cheap beer any night of the week, and a few times a month, the graduate Creative Writing program hosts its reading series here: poets and writers from one of the top five PhD programs in creative writing in the US come and read or perform their work for the crowd.

Tallahassee up and coming international bookmine

On the other end of Gaines, between Railroad Square and the new College Town area, is a Tallahassee classic: the International Bookmine. It looks like the perfect place to hole up when the Soviets finally come, but inside it has the shabby charm and woody smell of any good used book store. It might not be around all that much longer, but we’ll get to that.

College Town

As you follow west towards the stadium from the Railroad Square neighborhood, you’ll emerge in the newly constructed College Town, the crown jewel of Tallahassee’s recent development initiative. It’s promoted throughout the city, and rightfully so: the Leon County Community Redevelopment Agency projects the taxable value of the new development to be $15.5 million, an increase of $14.3 million (!!) over its 2012 value before the project began.

Tallahassee up and coming apartments

Some of the colorful new housing developments along Gaines.

This development has one target audience in mind: wealthier college students. Rentals here start at $750-$790 a month for one room in a three-bedroom apartment, and prices rise steeply from there. Madison Social is the entertainment hub of the area, restaurant by day, student bar by night, and from what I’ve seen the three times I’ve been, the crowd there reflects the demographic of College Town and college towns.

All along Madison Street are other places to have a beer, a coffee, or a meal, from frozen yogurt to live music and craft brews and the Brass Tap.

Tallahassee up and coming college town

Some of the construction on Phase 2 of the College Town development.

This seems like a great project, but I hope as development continues into phase 2, it’ll take into account the skyrocketing rent prices that’ll force out many of this area’s residents and small business owners. It’ll also be sort of misanthropically interesting to see what happens as this very plastic neighborhood collides with its hipster neighbor in Railroad Square just a few blocks down the road, likely provoking a territorial war between these natural enemies.

Downtown and Florida State University

Downtown Tallahassee has never been one of the Great American Downtowns, but I think now it’s at least climbing the ranks of great Floridian ones. There’s a good mix of budget-friendly and budget-breaking here, with a few fancier restaurants and bars balanced out by places like 101, whose happy hour special puts a vacant boozey smile on even the brokest college student’s face.

Tallahassee up and coming globe

One of the floats in this year’s Homecoming parade, from the Center for Intensive English Studies.

It’s hard to deny that most of the western side of Downtown Tallahassee is dominated by Florida State University and the associated college culture. Between the university and the State Capitol are all the fratty bars and clubs you could hope for, with upscale establishments like Potbelly’s, where twenty-year-old bros engage in yelling contests in the hopes of winning the affection of the females, just like on the Discovery Channel.

But the college scene is more than Greek life. FSU adds an international dimension that Tallahassee otherwise lacks, with regular events like International Coffee Hour at the Globe. You’ll be surprised by how many different international clubs and cultures you can find on FSU campus.

Tallahassee up and coming integration statue

Did I mention Florida State is the most beautiful university campus in the US? Fact.

Further into Downtown proper, where the state politicians play, Metro Deli is a good place to stop for an affordable lunch on a pleasant but not too busy urban street. By night, the cluster of bars and restaurants on Adams Street south of College is a good option for a mid-range night out: if you’re careful you can get out of Andrew’s Bar and Grill for under $15 and head next door to Clyde’s and Costello’s for a divey atmosphere, occasional live music, and a cheap beer.

Even better — actually, in my expert opinion, the absolute best — for a life-changing meal in Tallahassee is Wells Brothers Bar and Grill, locally known as Monk’s. It’s been voted best burger in Tallahassee every year since just before Christ was born, and their success has led to their opening a new restaurant in Midtown in the middle of the boom.



When I lived in Tallahassee, I always took my Couchsurfers to Monk’s, and I’ve got at least three Couchsurfing references that specifically mention those burgers as one of the highlights of their stay in Tallahassee. And to top it all off, I used to work at the bank where these guys did business, and they were always super cool, friendly, down to earth folks. Monk’s is the epitome of the kind of awesome small business you want in your town.

If you’re not a college student, you might wanna do more than gorge yourself and get drunk all day (I’ve heard). My personal favorite new downtown development for walking off the burgers and booze is Cascades Park, comfortably squeezed between the Capitol and Florida Agricultural and Mechanical University (FAMU), right in the geographic center of Tallahassee. It’s the first sizeable park in the Downtown area, and it even features the new Capital City Amphitheatre, a beautiful setting for an outdoor concert.

Tallahassee up and coming amphitheatre

The new Capital City Amphitheatre in Cascades Park.

Proof is another one dear to my heart, Tallahassee’s first decent beer bar, with good vibes and great selections. If you’re passing through the States and feeling nostalgic for some good Belgian or English beers, this place is almost certain to have what you’re looking for (it might cost six or eight bucks, but that’s kind of worth it in the land of Budweiser).



Also growing during the current boom, Proof now has a brewery open in Railroad Square, along with a tasting room and outdoor beer garden. I didn’t make it here on my recent trip, but according to their website, it’s got “live music, bocce ball, table tennis, and other entertaining outdoor activities.” The great thing about Proof is the demographic: basically everyone. It’s strictly 21-and-up, so no getting puked on by teenagers, and the crowd ranges from fraternities and sororities to grad students, to young professionals, to the odd university administrator, to people who just really like beer.

Newton’s third law of urban development

Everyone loves a new live music venue or a colorful new housing establishment, but don’t forget: for every action, there is an equal and opposite reaction.

The thing I love the most about all this is that my favorite local small businesses are kicking ass. Proof and Monk’s together constituted 68% of my monthly spending in college, so the fact that I can now give them my money in every corner of the city is kind of gratifying. I’ve seen other local Tallahassee businesses growing and expanding too, like the new Haute Headz salon in College Town, and others, like the iconic Lucy and Leo’s Cupcakery, are holding strong against the sudden onslaught of chain stores and other new competitors.

But it’s not all good news. Cherished businesses like the International Bookmine are financially threatened by the new developments, and realistically probably won’t make it much longer. Additionally, some areas — particularly in and around College Town — will be subject to increased crime caused by gentrification. For the stable young professional, the pretty new buildings on Gaines and Madison make us think of having an iced latte on the terrace during our lunch breaks, but this is where the equal and opposite reaction comes in.

Tallahassee up and coming graffiti

As rents rise, those at the bottom who were just barely making ends meet are suddenly not even close. Within the course of a few years, an entire neighborhood can be uprooted and displaced (which are really just euphemisms for ‘made homeless’).

But this doesn’t have to be the case; if Tallahassee invests in all of its population, the future is bright.

One overall win for Tallahassee’s urban development is Cascades Park. This kind of public spending normally goes where the money lives, but this new multi-purpose outdoor area is in one of the parts of town with the lowest average incomes and most minority residents, and I have to say sincerely that was really beautifully visible to me when I went there on a Sunday afternoon. Particularly in the corner of the park with jungle gyms and other things for the kids, I was overwhelmed by all the families of visibly different social class and race sitting and chatting on benches and making small talk as they walked their dogs past each other on the trail. I tend to think this park isn’t such a rainbow-colored utopia all day every day, but it was nice and frankly shocking for me to see in a city like Tallahassee and times like these.

I made light of some of the social stratification among students earlier, but Tallahassee has one of the worst, if not the absolute worst, divisions between rich and poor in the United States. State government higher-ups, university professors, middle class students, and, yes, wealthy retirees, have all staked out their own territories in Tallahassee, and what remains for working class Tallahasseeans in general is the most economically isolated leftovers.

Tallahassee up and coming cascades park

That said, Cascades Park’s location near historically black Florida A&M University and within reasonable distance of Frenchtown and some of the poorer Southside neighborhoods is by no means a cure-all, but it’s a step in the right direction. Economic inequality is a leading cause of crime, but building a sense of community among residents is one of the best-known deterrents, so constructing common spaces for the public good in lower-income areas is absolutely a good thing. One tactfully placed park is not a pattern, but it is a reason for a little optimism.

No one knows how the rest of Tallahassee’s boom will play out, if it’ll end up a well-kept secret of Florida and the Gulf Coast or a national capital of coolness, but you need to put on your hipster hat and go check it out before Tallahassee grows up into the next big thing.

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  1. James · December 23, 2015

    I’ve lived in Tallahassee for over a decade and I agree with most of your observations, although I think the city still has ways to go with development. In the past 2-3 years, I also began to notice the substantial growth of local businesses, FSU and FAMU, and the public sector. There is now a large variety of restaurants to eat and trendy nightlife spots to keep young professionals and students happy. The completion of Cascades Park and other parks/green spaces is making the city more aesthetically pleasing than ever before. It is also good to see older places being updated rather being demolished (examples: Tallahassee Mall renovations, Edison Restaurant, CRMC, various state buildings, etc…). Anyways, thank you for the article!

  2. Matthew · December 23, 2015

    I’m ambivalent about whether I want Tallahassee and the region of the Gulf Coast that abuts us discovered. On the one hand, this is the most biodiverse place in America–nature and the wildlife around us are glorious. People complain, but our weather and the topography are awesome. On the other hand, a lot of the unspoiled beauty of the Gulf Coast and places around us grows from their lack of development, the dire poverty that inheres there. Tallahassee often reminds me of Ann Arbor, town where I went to college, regularly cited as one of the hippest places in the country. . . as Ann Arbor was 15-20 years ago. But the poor and middle class people who gave Ann Arbor its flavor can no longer afford the town (like San Francisco). For my $ those places can be more annoying than appealing these days. Can we keep Tallahassee edgy, create jobs here, or will hip only ever mean spending two dollars more for your coffee at the Catalina rather than All Saints Cafe, not being clued in enough to figure out which one is the richer experience? Tallahassee has been waiting to explode–as the state capital, beautifully situated, it’s only a matter of time (a lot of knowing people already concede that this is the most appealing place in Florida). But our problems are serious–having the most economically segregated city in the country is no laughing matter. Jeb Bush cutting the state workforce by 8% hit Tallahassee, and the working class in Tallahassee, very, very hard. The five counties around us have a higher infant mortality rate than El Salvador and the liberal intelligentsia here, as in so many college towns, barely connects to local problems (when it is not openly disdainful, yearning to be elsewhere). FSU remains a very conservative institution, its gaze–like that of many universities–trained on solving the problems of the world when it can’t even focus on or fix the town where it’s situated. While local pols throw millions at restaurants that no poor people will ever set foot in, they devote a lot less to grassroots development. A great deal of our hope for the future lies in whether we can develop a LOCAL economy. Tune in 4-5 years from now, and let’s see whether the new Frenchtown Heritage Market and Food Hub are thriving–being supported by all these discerning professionals. For now we have one of the highest %s of people eating bad fast food in the country. . . .