Five Squared’s Guide to Lexington and Environs
Food Scene
Artsy, swanky restaurant serving upscale, Kentucky-based cuisine in one of the coolest boutique hotels in the country (thank you for choosing our Airbnb instead of staying there!). The restaurant bar is cool, too.
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Lockbox
167 W Main StArtsy, swanky restaurant serving upscale, Kentucky-based cuisine in one of the coolest boutique hotels in the country (thank you for choosing our Airbnb instead of staying there!). The restaurant bar is cool, too.
Our favorite Thai place in Lexington. Always easy to get a table. Try the pineapple curry with tofu and the pad kee mow.
Mai Thai Restaurant
304 Southland DrOur favorite Thai place in Lexington. Always easy to get a table. Try the pineapple curry with tofu and the pad kee mow.
Our favorite Indian restaurant in Lexington. Great lunch buffet, too.
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Masala Indian Cuisine
3061 Fieldstone WayOur favorite Indian restaurant in Lexington. Great lunch buffet, too.
This little joint is in a converted gas station. Locally sourced ingredients. Get some beignets!
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doodles breakfast and lunch
262 N LimestoneThis little joint is in a converted gas station. Locally sourced ingredients. Get some beignets!
Yes, it's an $11 salad, but it's really good — so much so that people are known to become obsessed with it for lunch. Part of a little local chain, they also serve great soups and the drinks are either organic ice tea or a variety of flavored lemonades.
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Vinaigrette Salad Kitchen
113 N BroadwayYes, it's an $11 salad, but it's really good — so much so that people are known to become obsessed with it for lunch. Part of a little local chain, they also serve great soups and the drinks are either organic ice tea or a variety of flavored lemonades.
Lots of folks agree that this is the best Mexican place in Lexington. A great mariachi band plays on Friday nights.
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El Rancho Tapatio
144 Burt RdLots of folks agree that this is the best Mexican place in Lexington. A great mariachi band plays on Friday nights.
A great little counter-service restaurant — owned by one of the Lexington's preeminent, James Beard Award-nominated chefs, Ouita Michel — in the middle of a bunch of horse farms. Quintessential Kentucky.
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Windy Corner Market
4595 Bryan Station RdA great little counter-service restaurant — owned by one of the Lexington's preeminent, James Beard Award-nominated chefs, Ouita Michel — in the middle of a bunch of horse farms. Quintessential Kentucky.
The sister restaurant of Windy Corner (below), it's also owned by one of the Lexington's preeminent, James Beard Award-nominated chefs, Ouita Michel, and has an equally picturesque setting.
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Wallace Station Deli and Bakery
3854 Old Frankfort PikeThe sister restaurant of Windy Corner (below), it's also owned by one of the Lexington's preeminent, James Beard Award-nominated chefs, Ouita Michel, and has an equally picturesque setting.
Quite possibly the best restaurant in Lexington. Serving pan-Latin tapas, it's owned and run by another prominent local chef, Jonathan Lundy. Try the chicken chicharron, queso blanco, papas en la latta, tres leches cake, caipirinha, and pretty much anything else on the menu.
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Corto Lima
101 W Short StQuite possibly the best restaurant in Lexington. Serving pan-Latin tapas, it's owned and run by another prominent local chef, Jonathan Lundy. Try the chicken chicharron, queso blanco, papas en la latta, tres leches cake, caipirinha, and pretty much anything else on the menu.
New restaurant in the renovated former Fayette County Courthouse. Modern take on Kentucky cuisine.
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Zim's Cafe
215 W Main StNew restaurant in the renovated former Fayette County Courthouse. Modern take on Kentucky cuisine.
Epping's on Eastside
264 Walton AveGreat place for a nice dinner out.
If you want a fancy steakhouse, pick this classy restaurant over rival Jeff Ruby’s or the subpar Malone’s.
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Tony's of Lexington
401 W Main StIf you want a fancy steakhouse, pick this classy restaurant over rival Jeff Ruby’s or the subpar Malone’s.
Award-winning chef Ouita Michel’s original restaurant is a nice, short drive from Lexington in picturesque Midway. Elevated Kentucky cuisine.
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Holly Hill Inn
426 N Winter StAward-winning chef Ouita Michel’s original restaurant is a nice, short drive from Lexington in picturesque Midway. Elevated Kentucky cuisine.
Divey restaurant with good food that’s very close to our place.
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Thoroughbred Restaurant
1483 Leestown RdDivey restaurant with good food that’s very close to our place.
One of James Beard-nominated chef Ouita Michel’s restaurants. Upscale Kentucky cuisine. Sitting in an outdoor mall, it’s among her most accessible places.
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Honeywood Restaurant
110 Summit At Fritz FarmOne of James Beard-nominated chef Ouita Michel’s restaurants. Upscale Kentucky cuisine. Sitting in an outdoor mall, it’s among her most accessible places.
Leestown Coffee House
1416 Leestown RdThe closest coffee place to our place. Locally owned.
Drinks & Nightlife
In the summer, this divey little gem's idyllic setting on the banks of Town Branch creek is worthy of a fairytale.
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The Break Room
1178 Manchester StIn the summer, this divey little gem's idyllic setting on the banks of Town Branch creek is worthy of a fairytale.
When the end of the world comes, the only things left will be cockroaches, Cher and The Bar Complex. It's been a gay bar since the 1950s, when Rock Hudson was known to visit; an unlikely disco palace in the 1970s and '80s with a dance floor designed by the Studio 54 peeps; and a drag revue in its most recent years. It's seen better days, but dip in here for a drink and a little LGBT history.
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The Bar Complex
224 E Main StWhen the end of the world comes, the only things left will be cockroaches, Cher and The Bar Complex. It's been a gay bar since the 1950s, when Rock Hudson was known to visit; an unlikely disco palace in the 1970s and '80s with a dance floor designed by the Studio 54 peeps; and a drag revue in its most recent years. It's seen better days, but dip in here for a drink and a little LGBT history.
Possibly one of the most amazing interior spaces in Lexington. A cavernous space with a huge bar inside a converted bourbon distillery. They serve great pizza, too.
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Goodfellas Distillery
1228 Manchester StreetPossibly one of the most amazing interior spaces in Lexington. A cavernous space with a huge bar inside a converted bourbon distillery. They serve great pizza, too.
The granddaddy of Lexington's burgeoning (and possibly oversaturated) local brewing scene. Personal fave: the West Sixth amber. While you're there, grab a bite from Smithtown Seafood, a little counter-service restaurant inside the taproom; it's owned by James Beard Award-nominated chef Ouita Michel.
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West Sixth Brewing
501 W 6th StThe granddaddy of Lexington's burgeoning (and possibly oversaturated) local brewing scene. Personal fave: the West Sixth amber. While you're there, grab a bite from Smithtown Seafood, a little counter-service restaurant inside the taproom; it's owned by James Beard Award-nominated chef Ouita Michel.
Parks & Nature
Lovely wide-open spaces, rolling hills, a nice playground, a huge dog park and riding stables
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Masterson Station Park
3051 Leestown RoadLovely wide-open spaces, rolling hills, a nice playground, a huge dog park and riding stables
The state botanical garden is a popular destination for communing with nature. Check out the native plants, go for a walk on the myriad trails, or take your kids to the great Children's Garden.
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The Arboretum, State Botanical Garden of KY
500 Alumni DrThe state botanical garden is a popular destination for communing with nature. Check out the native plants, go for a walk on the myriad trails, or take your kids to the great Children's Garden.
The place where, legend has it, Lexington was founded. It's a lovely little nature park unfortunately surrounded by industrial businesses; you might think you're lost getting there.
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McConnell Springs
416 Rebmann LnThe place where, legend has it, Lexington was founded. It's a lovely little nature park unfortunately surrounded by industrial businesses; you might think you're lost getting there.
Elkhorn Creek is one of the most beautiful waterways around, and Canoe Kentucky can help you explore it.
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Canoe Kentucky
7323 Peaks Mill RdElkhorn Creek is one of the most beautiful waterways around, and Canoe Kentucky can help you explore it.
Raven Run Náttúruverndarsvæði
3885 Raven Run WyLots of hiking trails bordering the Kentucky River.
STUNNING (all caps intended) nature area with jaw-dropping cliffs (known as a world-class rockclimbing destination), a natural bridge, hiking trails, etc. It's a hike (pun intended) from Lexington, but if you're in the area for a while and you love nature, this is a must-do.
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Red River Gorge
STUNNING (all caps intended) nature area with jaw-dropping cliffs (known as a world-class rockclimbing destination), a natural bridge, hiking trails, etc. It's a hike (pun intended) from Lexington, but if you're in the area for a while and you love nature, this is a must-do.
Arts & Culture
Home of Studio Players, the oldest community theater troupe in Kentucky. A gem.
Studio Players at The Carriage House Theatre
154 W Bell CtHome of Studio Players, the oldest community theater troupe in Kentucky. A gem.
Gorgeous turn-of-the-last-century performance hall that hosts touring Broadway shows, concerts and more.
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Lexington Opera House
401 W Short StGorgeous turn-of-the-last-century performance hall that hosts touring Broadway shows, concerts and more.
Check out the free contemporary art galleries on the first and second floors of this boutique hotel.
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21c Museum Hotel Lexington
167 W Main StCheck out the free contemporary art galleries on the first and second floors of this boutique hotel.
Lexington's most significant art museum, tucked inside the Singletary Center for the Arts. Photography exhibits are especially well-done.
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University of Kentucky Art Museum
405 Rose StLexington's most significant art museum, tucked inside the Singletary Center for the Arts. Photography exhibits are especially well-done.
Well-regarded, fully professional theater that produces work for children, including some original, commissioned works. A Lexington gem.
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Lexington Children's Theatre
418 W Short StWell-regarded, fully professional theater that produces work for children, including some original, commissioned works. A Lexington gem.
A replica of the home where legendary statesman and Lexingtonian Henry Clay lived. The house is kinda meh, but the grounds are lovely.
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Ashland - The Henry Clay Estate
120 Sycamore RdA replica of the home where legendary statesman and Lexingtonian Henry Clay lived. The house is kinda meh, but the grounds are lovely.
Home of the Lexington Philharmonic, touring concerts and University of Kentucky-produced events.
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Otis A. Singletary Center for the Arts
405 Rose StHome of the Lexington Philharmonic, touring concerts and University of Kentucky-produced events.
The Burl
375 Thompson RdGreat live music in a cozy Distillery District spot
The premier community theater group in the region. The productions are often on par with professional troupes.
Woodford Theatre
275 Beasley RdThe premier community theater group in the region. The productions are often on par with professional troupes.
Essentials
The full-service grocery nearest our rental. Recently expanded. Has a Starbucks inside.
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Kroger
704 Euclid AveThe full-service grocery nearest our rental. Recently expanded. Has a Starbucks inside.
Whole Foods Market
4059 Finn WyYou know what this is.
Leestown Wine and Spirits
1499 Leestown RdThe nearest liquor store to Five Squared.
The Little Clinic
1600 Leestown RdThe nearest walk-in medical clinic to Five Squared. Inside Kroger.
Sightseeing
Possibly the most beautiful bourbon distillery in Kentucky, where there are a lot of beautiful bourbon distilleries. Picturesque. Plus the whole place smells like bourbon.
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Woodford Reserve brennivínsvinnslan
7785 McCracken PikePossibly the most beautiful bourbon distillery in Kentucky, where there are a lot of beautiful bourbon distilleries. Picturesque. Plus the whole place smells like bourbon.
Was she crazy or just misunderstood? Find out at this small museum house celebrating the first lady and Lexington native.
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Mary Todd Lincoln House
578 W Main StWas she crazy or just misunderstood? Find out at this small museum house celebrating the first lady and Lexington native.
A whole park that celebrates horses and gets you access to some famous racing names. It's a working horse farm, too.
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Kentucky Hestapark
4089 Iron Works PkwyA whole park that celebrates horses and gets you access to some famous racing names. It's a working horse farm, too.
Why Panera? George Clooney — yes, THE George Clooney — was born in Lexington. Until he was about 3 years old, he lived in a house on the site of what is now a Panera Bread. True story.
Panera Bread
2887 Richmond RdWhy Panera? George Clooney — yes, THE George Clooney — was born in Lexington. Until he was about 3 years old, he lived in a house on the site of what is now a Panera Bread. True story.
Possibly Lexington's biggest draw for out-of-town visitors is this historic horseracing track, which has racing meets twice a year, in April and October. It's so picturesque (unlike most racetracks) that the movie Seabiscuit was filmed there. If you go, get decked out in your finest, wear a hat and get seats in the grandstand or, if you're connected, the clubhouse (general admission is for drunk college kids). Also check out the early Saturday morning event called Breakfast With the Works (which is fantastic for kids).
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Keeneland Race Track station
Possibly Lexington's biggest draw for out-of-town visitors is this historic horseracing track, which has racing meets twice a year, in April and October. It's so picturesque (unlike most racetracks) that the movie Seabiscuit was filmed there. If you go, get decked out in your finest, wear a hat and get seats in the grandstand or, if you're connected, the clubhouse (general admission is for drunk college kids). Also check out the early Saturday morning event called Breakfast With the Works (which is fantastic for kids).
This bourbon distillery is relatively new but it’s the nearest stop on the Bourbon Trail to our Airbnb. What it lacks in ambience and old-Kentucky authenticity, it makes up for in proximity.
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Town Branch Distillery
401 Cross StThis bourbon distillery is relatively new but it’s the nearest stop on the Bourbon Trail to our Airbnb. What it lacks in ambience and old-Kentucky authenticity, it makes up for in proximity.
It’s not the prettiest distillery near our place (that’d be Woodfore Reserve) but it’s likely the coolest. Unlike the tours at some places, here you will get thisclose to the action of a major distillery’s daily workings.
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Buffalo Trace brennivínsvinnslan
113 Great Buffalo TrceIt’s not the prettiest distillery near our place (that’d be Woodfore Reserve) but it’s likely the coolest. Unlike the tours at some places, here you will get thisclose to the action of a major distillery’s daily workings.
Where else but in Kentucky can you visit a retirement home for horses?
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Old Friends Farm
1841 Paynes Depot RdWhere else but in Kentucky can you visit a retirement home for horses?
Beautiful, recently restored distillery on the banks of Glenns Creek.
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Castle & Key brennivínsvinnslan
4445 McCracken PikeBeautiful, recently restored distillery on the banks of Glenns Creek.
If you’re a Backstreet Boys fan, you might know that members Brian Littrell and Kevin Richardson were born in Lexington. But did you know that this church is where Brian first sang publicly? Fact.
Porter Memorial Baptist Church
4300 Nicholasville RoadIf you’re a Backstreet Boys fan, you might know that members Brian Littrell and Kevin Richardson were born in Lexington. But did you know that this church is where Brian first sang publicly? Fact.
Entertainment & Activities
GORGEOUS 1920s movie theater that was recently restored. Seeing a movie here is a real treat.
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Kentucky Theatre
214 E Main StGORGEOUS 1920s movie theater that was recently restored. Seeing a movie here is a real treat.
See a University of Kentucky men's basketball game or a touring concert.
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Rupp Arena
430 W Vine StSee a University of Kentucky men's basketball game or a touring concert.