Caroline's Lexington Guidebook

Caroline
Caroline's Lexington Guidebook

Food scene

Great food, bar, and atmosphere with patio dining available
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Carson's Food & Drink
362 E Main St
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Great food, bar, and atmosphere with patio dining available
Awesome location in the distillery district right down the street from the home. Has a speakeasy vibe inside with patio dining and games available. Also good for dining on a budget.
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Goodfellas Distillery
1228 Manchester Street
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Awesome location in the distillery district right down the street from the home. Has a speakeasy vibe inside with patio dining and games available. Also good for dining on a budget.
Downtown Lexington’s premier local stake house is the perfect place to celebrate your special event or anniversary. They offer live music on weekends and are within walking distance of the AirBnb
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Tony's of Lexington
401 W Main St
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Downtown Lexington’s premier local stake house is the perfect place to celebrate your special event or anniversary. They offer live music on weekends and are within walking distance of the AirBnb
Literally right around the corner from the AirBnb, this is the closest distillery tour available. It’s definite a must-see if you’re interested in the process of bourbon making, or bourbon tasting!
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Town Branch Distillery
401 Cross St
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Literally right around the corner from the AirBnb, this is the closest distillery tour available. It’s definite a must-see if you’re interested in the process of bourbon making, or bourbon tasting!
Boasting one of Kentucky’s finest bourbons, and situated in between acres of horse farm, nothing says quintessential Kentucky like Woodford Reserve Distillery. Check out the new gift shop for souvenirs!
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Woodford Reserve Distillery
7785 McCracken Pike
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Boasting one of Kentucky’s finest bourbons, and situated in between acres of horse farm, nothing says quintessential Kentucky like Woodford Reserve Distillery. Check out the new gift shop for souvenirs!
Drop everything and get to Spaldings for the tastiest donuts imaginable. Seriously. They tend to stick to the basics- no wild experimental flavors here but their cream filled and chocolate glazed donuts will have you planning your next trip to Lexington. No dine-in. Cash only!
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Spalding's Bakery
760 Winchester Rd
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Drop everything and get to Spaldings for the tastiest donuts imaginable. Seriously. They tend to stick to the basics- no wild experimental flavors here but their cream filled and chocolate glazed donuts will have you planning your next trip to Lexington. No dine-in. Cash only!
Great local dining (started out as a successful food truck!) in the distillery district, down the street from the AirBnb
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middle fork kitchen bar
1224 Manchester St
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Great local dining (started out as a successful food truck!) in the distillery district, down the street from the AirBnb
One of my favorite brunches in town, Doodles sources all of their food from local farms and businesses, and makes some of the best beignets available north of Louisiana! Patio dining available
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doodles breakfast and lunch
262 N Limestone
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One of my favorite brunches in town, Doodles sources all of their food from local farms and businesses, and makes some of the best beignets available north of Louisiana! Patio dining available
Located in Lexington’s old courthouse just beside the visitor’s center, Zim’s offers casual brunch and lunch. This is the closest of renowned Chef Ouita Michel’s restaurants- I cannot recommend her group of niche local restaurants highly enough!
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Zim's Cafe
215 W Main St
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Located in Lexington’s old courthouse just beside the visitor’s center, Zim’s offers casual brunch and lunch. This is the closest of renowned Chef Ouita Michel’s restaurants- I cannot recommend her group of niche local restaurants highly enough!
The closest coffee shop to the house is less than a 5 minute walk and boasts a delicious beverage menu with a fun interior vibe
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Manchester Coffee Co.
903 Manchester St
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The closest coffee shop to the house is less than a 5 minute walk and boasts a delicious beverage menu with a fun interior vibe
Great food and atmosphere
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Distilled at The Sire
157 Jefferson St
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Great food and atmosphere
Award winning ice cream founded right here in Lexington. Also featuring ice cream cocktails and liqueurs
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Crank & Boom Ice Cream Lounge
1210 Manchester St
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Award winning ice cream founded right here in Lexington. Also featuring ice cream cocktails and liqueurs
Local brunch eatery with classic brunch foods and a cozy laid-back vibe.
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Josie's Restaurant
1973 Lexington Rd
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Local brunch eatery with classic brunch foods and a cozy laid-back vibe.
For rooftop views of the city while you sip, visit the Infinity sky bar and lounge located above the Marriott in the City Centre
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Infinity: A Skybar & Cafe
150 West Main Street
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For rooftop views of the city while you sip, visit the Infinity sky bar and lounge located above the Marriott in the City Centre
A local favorite bar with a rooftop patio in nice weather, stop by Belle’s for a cocktail
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Belles Cocktail House
156 Market St
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A local favorite bar with a rooftop patio in nice weather, stop by Belle’s for a cocktail
For some fresh dishes with south-of-the-border influence, try Corto Lima located downtown near the Lexington courthouse
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Corto Lima
101 W Short St
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For some fresh dishes with south-of-the-border influence, try Corto Lima located downtown near the Lexington courthouse
A local craft beer hotspot with a great tap house, West 6th has become iconic in the Lexington brewery scene
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West Sixth Brewing
501 W 6th St
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A local craft beer hotspot with a great tap house, West 6th has become iconic in the Lexington brewery scene
Within walking distance of the AirBnb and some of the best local brews around, Country Boy features a rustic tap house with a readily available food truck during high traffic hours
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Country Boy Brewing
436 Chair Ave
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Within walking distance of the AirBnb and some of the best local brews around, Country Boy features a rustic tap house with a readily available food truck during high traffic hours
Enjoy the best kombucha Lexington (or anywhere, for that matter) has to offer just a short trip from the AirBnb! Chat with the owners if they’re around- you won’t meet nicer people!
Thrive Kombucha
810 N Limestone
Enjoy the best kombucha Lexington (or anywhere, for that matter) has to offer just a short trip from the AirBnb! Chat with the owners if they’re around- you won’t meet nicer people!
Enjoy an array of dining, goods, and services at this newly repurposed historic bus station on the north side of town
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Greyline Station & Market
101 W Loudon Ave
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Enjoy an array of dining, goods, and services at this newly repurposed historic bus station on the north side of town
Really cool outdoor cafe on the grounds of one of Lexington’s oldest plant nurseries. An oasis of wooded garden situated downtown, they offer an array of local beers and pastries and a craft fair at Christmas
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Kentucky Native Café
417 E Maxwell St
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Really cool outdoor cafe on the grounds of one of Lexington’s oldest plant nurseries. An oasis of wooded garden situated downtown, they offer an array of local beers and pastries and a craft fair at Christmas
Best Mediterranean food anywhere. I crave food from this place. Get there early (like lunchtime) because they run our every day. Also closed much of the summer, so check on hours before you go!
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Sahara Mediterranean Cuisine
3061 Fieldstone Way
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Best Mediterranean food anywhere. I crave food from this place. Get there early (like lunchtime) because they run our every day. Also closed much of the summer, so check on hours before you go!
You can walk here from the Airbnb! Great tacos and funky decor make this a fun place to dine.
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Agave & Rye
123 North Broadway
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You can walk here from the Airbnb! Great tacos and funky decor make this a fun place to dine.
This place is a short walk away down high street just across from Rupp Arena. It has a movie theater, bowling, food, bar, and more! Great for kids or a date night.
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LexLive
301 S Broadway
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This place is a short walk away down high street just across from Rupp Arena. It has a movie theater, bowling, food, bar, and more! Great for kids or a date night.
A one-of-a-kind dining experience with local favorites nestled in between horse farms owned by renowned Chef Ouita Michael
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Windy Corner Market
4595 Bryan Station Rd
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A one-of-a-kind dining experience with local favorites nestled in between horse farms owned by renowned Chef Ouita Michael

Sightseeing

What to see and do in Lexington and the surrounding areas
A must-see if visiting Lexington in season. Our iconic horse racing track with local eats and drinks. Or walk the beautiful grounds if you missed the racing window!
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Keeneland
4201 Versailles Road
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A must-see if visiting Lexington in season. Our iconic horse racing track with local eats and drinks. Or walk the beautiful grounds if you missed the racing window!
The iconic home of UK Basketball team, you can catch a lot more than sports at this entertainment venue. Plan your trip around a show or concert.
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Rupp Arena
430 W Vine St
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The iconic home of UK Basketball team, you can catch a lot more than sports at this entertainment venue. Plan your trip around a show or concert.
History buffs-this one’s for you! See famous statesman and orator Henry Clay’s home and grounds. Tours of the interior are provided for a fee- check the website before you go for accurate pricing.
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Ashland - The Henry Clay Estate
120 Sycamore Rd
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History buffs-this one’s for you! See famous statesman and orator Henry Clay’s home and grounds. Tours of the interior are provided for a fee- check the website before you go for accurate pricing.
Known for its meticulous landscaping and diverse tree and plant population, the Lexington Cemetery makes an excellent place for a leisurely walk and can easily be accessed from the AirBnb.
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The Lexington Cemetery
833 W Main St
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Known for its meticulous landscaping and diverse tree and plant population, the Lexington Cemetery makes an excellent place for a leisurely walk and can easily be accessed from the AirBnb.
The local visitors center, situated inside the old courthouse, can offer more sightseeing ideas that I may have missed here!
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Lexington Visitors Center
215 W Main St
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The local visitors center, situated inside the old courthouse, can offer more sightseeing ideas that I may have missed here!
The Kentucky Horse Park is the heartbeat of Lexington. Hosting horse-themed events throughout the year, the Horse Park remains open year-round for tours and exhibits (International Museum of the Horse) and famous racehorse meet-and-greets!
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Kentucky Horse Park
4089 Iron Works Pkwy
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The Kentucky Horse Park is the heartbeat of Lexington. Hosting horse-themed events throughout the year, the Horse Park remains open year-round for tours and exhibits (International Museum of the Horse) and famous racehorse meet-and-greets!
Within walking distance of the AirBnb, you can tour the childhood home of our 16th president’s wife
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Mary Todd Lincoln House
578 W Main St
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Within walking distance of the AirBnb, you can tour the childhood home of our 16th president’s wife
A Lexington icon, the opera house provides an intimate setting for Broadway touring productions, professional theatrical performances, and local recitals
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Lexington Opera House
401 W Short St
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A Lexington icon, the opera house provides an intimate setting for Broadway touring productions, professional theatrical performances, and local recitals
A Lexington icon, this horse racetrack is a must-see for a first visit to Lexington. If you’re lucky enough to visit during racing season (April and October) place a bet on a pony, sip on some classic bourbon cocktails, and enjoy the sights of the area. It’s open year-round for visitors but check beforehand for special events.
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Keeneland Race Track station
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A Lexington icon, this horse racetrack is a must-see for a first visit to Lexington. If you’re lucky enough to visit during racing season (April and October) place a bet on a pony, sip on some classic bourbon cocktails, and enjoy the sights of the area. It’s open year-round for visitors but check beforehand for special events.
The Arboretum, State Botanical Garden of KY
500 Alumni Dr
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Shopping

For upscale shopping and dining, check out this new outdoor upscale mall on the South Side of Lexington
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The Summit at Fritz Farm
120 Summit At Fritz Farm
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For upscale shopping and dining, check out this new outdoor upscale mall on the South Side of Lexington
Hamburg is such a huge shopping center, I’m not sure how they could miss anything you’d need during your stay. Target, nail salons, Meijer grocery, movie theater, restaurants, fast food, etc.
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Hamburg Pavilion
2308 Sir Barton Way
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Hamburg is such a huge shopping center, I’m not sure how they could miss anything you’d need during your stay. Target, nail salons, Meijer grocery, movie theater, restaurants, fast food, etc.
Unique and quirky finds, elegant upscale consignment furniture, oriental rugs, original art- you’ll find all this and more at my favorite furniture store in Lexington. Scout neighbors many more antique and consignment furniture stores, if interested!
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Scout Antique & Modern
935 Liberty Rd
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Unique and quirky finds, elegant upscale consignment furniture, oriental rugs, original art- you’ll find all this and more at my favorite furniture store in Lexington. Scout neighbors many more antique and consignment furniture stores, if interested!
This is an easy walk from the AirBnb, and is open most Saturday mornings (check the website before you go). Stock up on fresh local produce, fresh flowers, kombucha, or jams/jellies to sample
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Lexington Farmers Market
399 W Short St
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This is an easy walk from the AirBnb, and is open most Saturday mornings (check the website before you go). Stock up on fresh local produce, fresh flowers, kombucha, or jams/jellies to sample
Lexington’s local bookstore surrounded by local shops and dining overlooking a large pond. Cozy up by their fireplace with a good read on a rainy day, or get lucky and meet the author at one of their frequent book signings
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Joseph-Beth Booksellers
161 Lexington Green Cir
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Lexington’s local bookstore surrounded by local shops and dining overlooking a large pond. Cozy up by their fireplace with a good read on a rainy day, or get lucky and meet the author at one of their frequent book signings
You can walk here from the Airbnb! And there are other cute shops in this Victorian Square neighborhood as well
Urban Outfitters
401 W Main St
You can walk here from the Airbnb! And there are other cute shops in this Victorian Square neighborhood as well

Neighborhoods

Pay a visit to Kentucky’s capitol if history and government capture your interest. 40 minutes up the interstate, Frankfort offsets it’s own small-town charm and Kentucky’s longest running distillery, Buffalo Trace
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Frankfort
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Pay a visit to Kentucky’s capitol if history and government capture your interest. 40 minutes up the interstate, Frankfort offsets it’s own small-town charm and Kentucky’s longest running distillery, Buffalo Trace
Quaint historic small town on the outskirts of Lexington with a notable dining scene (Holly Hill Inn) and antique stores to appreciate
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Midway
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Quaint historic small town on the outskirts of Lexington with a notable dining scene (Holly Hill Inn) and antique stores to appreciate
Great eats and historic homes make this a fun neighborhood stroll
Jefferson Street
Jefferson Street
Great eats and historic homes make this a fun neighborhood stroll

Recreation and Exercise

If you’re looking to break a sweat during your stay, these recommendations are for you
For those with a YMCA membership, the High Street Y is kind of a Lexington classic. She’s not state of the art, but she gets the job done (and offers a lap pool) and if you listen really closely, you can hear your mom’s 1980’s aerobics music faintly echoing through the halls
High Street YMCA
239 E High St
For those with a YMCA membership, the High Street Y is kind of a Lexington classic. She’s not state of the art, but she gets the job done (and offers a lap pool) and if you listen really closely, you can hear your mom’s 1980’s aerobics music faintly echoing through the halls
The Legacy Trail is a 12 mile out-and-back paved path perfect for biking, running, walking, or whatever you like to do on paved paths. It runs through farmland and ends at the Kentucky Horse Park. I recommend an early morning bike ride to catch the morning mist on the bluegrass!
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Legacy Trail
Legacy Trail
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The Legacy Trail is a 12 mile out-and-back paved path perfect for biking, running, walking, or whatever you like to do on paved paths. It runs through farmland and ends at the Kentucky Horse Park. I recommend an early morning bike ride to catch the morning mist on the bluegrass!
A hidden outdoor gem close to the AirBnb, McConnell Springs features wooded hiking trails and a nature center kids and adults can appreciate! Free to visit.
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McConnell Springs
416 Rebmann Ln
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A hidden outdoor gem close to the AirBnb, McConnell Springs features wooded hiking trails and a nature center kids and adults can appreciate! Free to visit.
Great hiking trails with scenic overlook and a nature center perfect for families. Free entry! Located about 25 minute drive from the AirBnb.
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Raven Run Nature Sanctuary
3885 Raven Run Wy
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Great hiking trails with scenic overlook and a nature center perfect for families. Free entry! Located about 25 minute drive from the AirBnb.
Located about 1 hour east of Lexington, RRG offers some of the best hiking and rock climbing in the region. Plan on a full day here- there’s plenty to do and even some great eats nearby (Miguel’s 🍕)
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Red River Gorge
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Located about 1 hour east of Lexington, RRG offers some of the best hiking and rock climbing in the region. Plan on a full day here- there’s plenty to do and even some great eats nearby (Miguel’s 🍕)
Young kids will enjoy the offerings of Lexington’s only children’s museum. Ideal for half-day, particularly when weather limits outdoor activities!
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Explorium of Lexington
440 W Short St
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Young kids will enjoy the offerings of Lexington’s only children’s museum. Ideal for half-day, particularly when weather limits outdoor activities!

Råd om byen

Skikke og kultur

Personal car/Uber is usually the best way to get around

There is plenty to see and do within walking distance of the home, but don’t miss out on some of the best Lexington has to offer- much of which requires vehicle transport
Book, inden du rejser

Distillery tours

Sign up in advance for our bourbon distillery tours, particularly in Keeneland season (May and October) as these tend to fill up months in advance!