Five Squared’s Guide to Lexington and Environs

Scott
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.
20 当地人推荐
Lockbox
167 W Main St
20 当地人推荐
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.
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 Dr
Our 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.
7 当地人推荐
Masala Indian Cuisine
3061 Fieldstone Way
7 当地人推荐
Our favorite Indian restaurant in Lexington. Great lunch buffet, too.
This little joint is in a converted gas station. Locally sourced ingredients. Get some beignets!
38 当地人推荐
doodles breakfast and lunch
262 N Limestone
38 当地人推荐
This 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.
16 当地人推荐
Vinaigrette Salad Kitchen
113 N Broadway
16 当地人推荐
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.
Lots of folks agree that this is the best Mexican place in Lexington. A great mariachi band plays on Friday nights.
13 当地人推荐
El Rancho Tapatio
144 Burt Rd
13 当地人推荐
Lots 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.
55 当地人推荐
Windy Corner Market
4595 Bryan Station Rd
55 当地人推荐
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.
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.
66 当地人推荐
Wallace Station Deli and Bakery
3854 Old Frankfort Pike
66 当地人推荐
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.
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.
62 当地人推荐
Corto Lima
101 W Short St
62 当地人推荐
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.
New restaurant in the renovated former Fayette County Courthouse. Modern take on Kentucky cuisine.
24 当地人推荐
Zim's Cafe
215 W Main St
24 当地人推荐
New restaurant in the renovated former Fayette County Courthouse. Modern take on Kentucky cuisine.
Great place for a nice dinner out.
24 当地人推荐
Epping's on Eastside
264 Walton Ave
24 当地人推荐
Great 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.
95 当地人推荐
Tony's of Lexington
401 W Main St
95 当地人推荐
If 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.
26 当地人推荐
Holly Hill Inn
426 N Winter St
26 当地人推荐
Award-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.
8 当地人推荐
Thoroughbred Restaurant
1483 Leestown Rd
8 当地人推荐
Divey 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.
10 当地人推荐
Honeywood Restaurant
110 Summit At Fritz Farm
10 当地人推荐
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.
The closest coffee place to our place. Locally owned.
Leestown Coffee House
1416 Leestown Rd
The 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.
17 当地人推荐
The Break Room
1178 Manchester St
17 当地人推荐
In 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.
12 当地人推荐
The Bar Complex
224 E Main St
12 当地人推荐
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.
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.
80 当地人推荐
Goodfellas Distillery
1228 Manchester Street
80 当地人推荐
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.
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.
152 当地人推荐
West Sixth Brewing
501 W 6th St
152 当地人推荐
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.

Parks & Nature

Lovely wide-open spaces, rolling hills, a nice playground, a huge dog park and riding stables
14 当地人推荐
马斯特森站公园
3051 Leestown Road
14 当地人推荐
Lovely 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.
97 当地人推荐
肯塔基州立植物园的树木园
500 Alumni Dr
97 当地人推荐
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.
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.
43 当地人推荐
McConnell Springs
416 Rebmann Ln
43 当地人推荐
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.
Elkhorn Creek is one of the most beautiful waterways around, and Canoe Kentucky can help you explore it.
23 当地人推荐
Canoe Kentucky
7323 Peaks Mill Rd
23 当地人推荐
Elkhorn Creek is one of the most beautiful waterways around, and Canoe Kentucky can help you explore it.
Lots of hiking trails bordering the Kentucky River.
107 当地人推荐
Raven Run Nature Sanctuary
3885 Raven Run Wy
107 当地人推荐
Lots 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.
185 当地人推荐
Red River Gorge
185 当地人推荐
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 Ct
Home 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.
65 当地人推荐
Lexington Opera House
401 W Short St
65 当地人推荐
Gorgeous 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.
32 当地人推荐
21c Museum Hotel Lexington
167 W Main St
32 当地人推荐
Check 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.
14 当地人推荐
University of Kentucky Art Museum
405 Rose St
14 当地人推荐
Lexington'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.
7 当地人推荐
Lexington Children's Theatre
418 W Short St
7 当地人推荐
Well-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.
86 当地人推荐
Ashland - The Henry Clay Estate
120 Sycamore Rd
86 当地人推荐
A 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.
11 当地人推荐
Otis A. Singletary Center for the Arts
405 Rose St
11 当地人推荐
Home of the Lexington Philharmonic, touring concerts and University of Kentucky-produced events.
Great live music in a cozy Distillery District spot
73 当地人推荐
The Burl
375 Thompson Rd
73 当地人推荐
Great 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 Rd
The 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.
96 当地人推荐
Kroger
704 Euclid Ave
96 当地人推荐
The full-service grocery nearest our rental. Recently expanded. Has a Starbucks inside.
You know what this is.
20 当地人推荐
Whole Foods Market
4059 Finn Wy
20 当地人推荐
You know what this is.
The nearest liquor store to Five Squared.
Leestown Wine and Spirits
1499 Leestown Rd
The nearest liquor store to Five Squared.
The nearest walk-in medical clinic to Five Squared. Inside Kroger.
The Little Clinic
1600 Leestown Rd
The 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.
221 当地人推荐
Woodford Reserve Distillery
7785 McCracken Pike
221 当地人推荐
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.
Was she crazy or just misunderstood? Find out at this small museum house celebrating the first lady and Lexington native.
70 当地人推荐
Mary Todd Lincoln House
578 W Main St
70 当地人推荐
Was 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.
329 当地人推荐
肯塔基马场
4089 Iron Works Pkwy
329 当地人推荐
A 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 Rd
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.
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).
246 当地人推荐
Keeneland Race Track station
246 当地人推荐
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.
79 当地人推荐
Town Branch Distillery
401 Cross St
79 当地人推荐
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.
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.
166 当地人推荐
Buffalo Trace Distillery
113 Great Buffalo Trce
166 当地人推荐
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.
Where else but in Kentucky can you visit a retirement home for horses?
48 当地人推荐
Old Friends Farm
1841 Paynes Depot Rd
48 当地人推荐
Where else but in Kentucky can you visit a retirement home for horses?
Beautiful, recently restored distillery on the banks of Glenns Creek.
76 当地人推荐
Castle & Key Distillery
4445 McCracken Pike
76 当地人推荐
Beautiful, 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 Road
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.

Entertainment & Activities

GORGEOUS 1920s movie theater that was recently restored. Seeing a movie here is a real treat.
67 当地人推荐
Kentucky Theatre
214 E Main St
67 当地人推荐
GORGEOUS 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.
140 当地人推荐
Rupp Arena
430 W Vine St
140 当地人推荐
See a University of Kentucky men's basketball game or a touring concert.