Lexington

"Saddle up in Lexington, where the equestrian world and Kentuckyโ€™s rolling hills intertwine."

๐ŸŽ๐ŸŒฟ๐Ÿ‡

Currency

US Dollar (USD) $

Best Time

Mar โ€“ Nov

Population

325,000

Weather ยฐC

5-28ยฐC

TWYS โ€” The Best Travel Guides for Hidden Gems & Local Secrets

Lexington is the heart of Kentuckyโ€™s horse-racing tradition, offering unparalleled access to the world of thoroughbred breeding and racing. The city is surrounded by scenic Bluegrass Country, which is perfect for hiking, biking, and outdoor activities. As one of the worldโ€™s foremost destinations for equestrian events, Lexington draws both seasoned horse racing fans and newcomers alike. Additionally, the city is rich in bourbon heritage, offering tours of distilleries that produce some of the finest whiskey in the world.
Year

1775 AD American colonial era, known for the Battle of Lexington during the American Revolution.

Cost of Living (10)

6๏ธโƒฃ Affordable, with a lower cost of living than many larger U.S. cities.

State

Kentucky

Airport

Blue Grass Airport (LEX)

boutique shopping

Minimal List TL;DR

TWYS curates the best places to SEE, EAT, DRINK, SHOP & MORE โ€” uncover hidden gems, must-visit landmarks, top restaurants, unique bars, boutique shops, luxury stays, and networking spots.

Shop
Market
๐Ÿฅ•

Lexington Farmers Market

4.8
A great way to experience local culture
Shop
Vintage Store
๐Ÿ›๏ธ

The Green Room

4.7
A treasure trove for vintage finds
Shop
Farmers Market
๐Ÿ…

Southland Drive Farmers Market

4.6
A community favorite
Shop
Boutique
๐Ÿ›๏ธ

The Lyric Theatre & Cultural Arts Center

4.5
A cultural gem in the heart of Lexington
See
Botanical Garden
๐ŸŒบ

The Arboretum

4.8
A peaceful retreat in the city
See
Historic Site
๐Ÿฐ

The Hunt-Morgan House

4.6
A key historical landmark
See
Historic District
๐Ÿ˜๏ธ

Gratz Park Historic District

4.6
A stroll through history
See
Historical Site
๐Ÿ›

Mary Todd Lincoln House

4.6
A significant piece of American history
See
Nature
๐ŸŒณ

Raven Run Nature Sanctuary

4.6
A hidden gem for outdoor enthusiasts
See
Farm
๐Ÿ„

Old Friend Farm

4.6
Educational and fun for all ages
See
Historic Site
๐Ÿ›

The Lexington Opera House

4.5
A cultural landmark
See
Art Gallery
๐ŸŽจ

The Living Arts & Science Center

4.5
A creative hub for learning
Eat
Cafรฉ
โ˜•

Crank & Boom Ice Cream

4.9
Perfect for dessert lovers
Eat
Restaurant
๐Ÿฝ

J. Render's Southern Table

4.7
A local favorite for Southern cuisine
Eat
Cafรฉ
โ˜•

Third Street Stuff

4.6
A local hangout spot
Eat
Food Truck
๐Ÿด

The Grateful Dog

4.5
Fun dining experience
Drink
Brewery
๐Ÿบ

West Sixth Brewing

4.8
A must-visit for craft beer lovers
Drink
Distillery
๐Ÿฅƒ

Bluegrass Distillers

4.7
A unique experience for bourbon aficionados
Drink
Winery
๐Ÿท

Equus Run Vineyard

4.6
Perfect for wine enthusiasts

Places to See

Discover breathtaking landmarks, hidden gems, and offbeat sights that make every destination unforgettable.

Must Visit:

Horse Racing, Bourbon Distillery Tours, Kentucky Derby, Scenic Countryside, Historical Landmarks. Lexington is famous for its horse racing, bourbon distillery tours, and the annual Kentucky Derby, making it a must-visit for fans of equestrian culture.

Lexington, the heart of Kentuckyโ€™s Bluegrass region, is famous for its large thoroughbred horse industry and the largest thoroughbred auction in the U.S. The city is a haven for bourbon lovers, with numerous distilleries offering tours and tastings. It also hosts prestigious events like the Kentucky Horse Show and the Rolex Kentucky Three-Day Event. The surrounding landscape features rolling hills and picturesque horse farms, making it one of the most iconic destinations in the U.S. for equestrian enthusiasts.

local places to eat

Places to Eat

Savor the best local flavors, street food gems, and must-try dining spots curated for true food lovers.

Must Try:

๐Ÿ— Southern Fried Chicken (crispy and flavorful) ๐Ÿ– BBQ (smoked meats with tangy sauce) ๐Ÿน Bourbon (Kentuckyโ€™s signature drink) ๐Ÿž Biscuits (fluffy southern bread served with honey or gravy) ๐Ÿ” Hot Brown (open-faced sandwich with turkey, bacon, and cheese) ๐Ÿช Bourbon Balls (chocolate and bourbon treats)

Places to Drink

Unwind at vibrant bars, cozy cafรฉs, and craft breweries, handpicked for the best drinks and atmosphere.
Music & Dance:

๐ŸŽป Bluegrass (Bill Monroeโ€™s birthplace, bluegrass concerts) ๐ŸŽถ Country (a heart of Kentuckyโ€™s country music) ๐Ÿ’ƒ Appalachian Folk Music (traditional sounds with banjos and fiddles) ๐ŸŽธ Enjoy the sounds of the Appalachian Mountains in vibrant venues.

places to network

Places to Network

Connect with like-minded travelers, digital nomads, and entrepreneurs at the best networking spots.
We'll update more places soon!
Key Industries:

๐ŸŒพ Agriculture: Known as the "Horse Capital of the World," Lexington is famous for its horse breeding industry, producing world-class racehorses. ๐Ÿ‡ Horse Breeding: The region has a long history of equine breeding, with numerous farms and events supporting this sector. ๐Ÿด Equine Services: The cityโ€™s economy is bolstered by services such as veterinary care, training, and events like the Kentucky Derby.

Lexington

"Lexington, where every race and every racecourse tells a story of tradition and passion."
local places to shop

Places to Shop

Explore local markets, unique boutiques, and artisanal stores for one-of-a-kind finds.

luxury experiences

Luxury

Indulge in high-end experiences, exclusive stays, and premium services tailored for refined travelers.
For More Tips Read on Further...

Equestrian Lexington Life

Horse racing, scenic equestrian farms, historical significance, bourbon distilleries, and charming Southern ambiance.

Kyoto, known as Japanโ€™s cultural capital, is famous for its historic temples, stunning gardens, and traditional tea houses. The city is home to iconic sites like the Golden Pavilion (Kinkaku-ji), Fushimi Inari Shrine, and the Arashiyama Bamboo Grove. Kyoto also offers a unique glimpse into Japanโ€™s ancient customs, with its geishas, traditional crafts, and beautiful cherry blossoms in spring. Kyotoโ€™s tranquil atmosphere, combined with its rich history and culture, makes it a must-visit for those seeking to experience traditional Japan.

Lexington, Kentucky, known as the "Horse Capital of the World," is a city where equestrian culture, history, and southern hospitality come together. The city is famous for its thoroughbred horse racing industry, and visitors can tour renowned horse farms, attend the Kentucky Derby, and visit the Kentucky Horse Park, where they can learn about the world of horses and equestrian sports. Lexington is also known for its beautiful landscapes, including the nearby Bluegrass Region, which features rolling hills, picturesque pastures, and historic horse farms. In addition to its equestrian heritage, Lexington has a thriving food scene, with bourbon distilleries producing some of the finest spirits in the world. The cityโ€™s vibrant downtown area offers a mix of modern dining options, boutique shops, and historic landmarks, such as the Mary Todd Lincoln House and the Old State Capitol. Lexingtonโ€™s rich cultural heritage, combined with its contemporary vibe, makes it a unique destination for visitors seeking both history and modern experiences. Whether you're visiting for the horses, bourbon, or vibrant culture, Lexington offers something for everyone.

watch out for these things

Watch Out

Watchย out for Crowded Areas

Avoid overrated tourist traps and discover alternative experiences worth your time.

Skip Super Touristic Places

Off the beaten path places in

Lexington

Transportation

๐ŸšŒ The local bus system covers the city, with services to key neighborhoods. The Blue Grass Airport โœˆ๏ธ is nearby for domestic flights, and highways ๐Ÿš— connect to larger cities like Louisville and Cincinnati.

travel around within the city

City Overview

Lexington: The Horse Capital of the World Lexington, known as the Horse Capital of the World, is a city that celebrates its deep-rooted equine heritage. Famous for its thoroughbred horse racing, horse farms, and the prestigious Keeneland Racecourse, Lexington is a dream destination for horse enthusiasts and those looking to experience the grandeur of Kentuckyโ€™s bluegrass region. Beyond its equestrian appeal, Lexington offers a blend of Southern hospitality and cultural richness. The city is home to a number of historic landmarks, including Mary Todd Lincoln House and Ashland, the former estate of Henry Clay. Lexingtonโ€™s vibrant downtown area features a mix of art galleries, craft breweries, and boutiques, reflecting the cityโ€™s creative spirit. The nearby Bourbon Trail offers an immersive experience into one of Kentuckyโ€™s most iconic exportsโ€”bourbon. With its charming blend of history, culture, and nature, Lexington is a city where visitors can experience the elegance of the horse world while enjoying the beauty of the bluegrass countryside.

Lexington

3 Day City Guide

๐ŸŒ… Day 1: ๐Ÿ•˜ Morning: Visit the Kentucky Horse Park ๐Ÿ‡. ๐Ÿ•› Afternoon: Explore the Mary Todd Lincoln House ๐Ÿ . ๐Ÿ•• Evening: Dinner at a local restaurant ๐Ÿฝ๏ธ. ๐ŸŒ‡ Day 2: ๐Ÿ•˜ Morning: Tour a horse farm ๐ŸŽ. ๐Ÿ•› Afternoon: Visit the Distillery District ๐Ÿถ. ๐Ÿ•• Evening: Attend a local live music event ๐ŸŽถ. ๐ŸŒ‡ Day 3: ๐Ÿ•˜ Morning: Explore the University of Kentucky campus ๐Ÿซ. ๐Ÿ•› Afternoon: Visit the Ashland estate ๐Ÿฐ. ๐Ÿ•• Evening: Enjoy a bourbon tasting ๐Ÿฅƒ.

Current Trends

๐Ÿฝ๏ธ Culinary Trends: A growing interest in farm-to-table dining, with an emphasis on fresh, local ingredients. ๐ŸŽ Eco-Tourism: A surge in horse-related tourism experiences, with tours and equestrian events. ๐ŸŽญ Cultural Events: Rising focus on local arts and music festivals, including the Lexington Opera House and WoodSongs Old-Time Radio Hour. ๐ŸŒฑ Sustainable Travel: A focus on eco-friendly tourism, including green hotels and energy-efficient transportation. ๐Ÿธ Bourbon Tourism: Lexington's bourbon industry continues to attract tourists with tours and tastings at historic distilleries.

Local Events Guide

๐Ÿฅƒ Kentucky Bourbon Festival (September): Celebrating the regionโ€™s rich bourbon heritage with tastings, distillery tours, and expert talks. ๐ŸŒˆ Lexington Pride Festival (June): A celebration of the LGBTQ+ community with performances, parades, and support for equality. ๐ŸŽถ Bluegrass Fair (July): Featuring local crafts, bluegrass music, and delicious food, this event is a celebration of southern culture. ๐Ÿ‡ The Lexington Horse Show (August): An equestrian event featuring competitive show jumping, dressage, and more. ๐Ÿ‡ Kentucky Wine and Music Festival (May): Celebrating Kentuckyโ€™s wine culture with live music and tastings from local wineries.

Local Insider Tips

๐Ÿ‡ Kentucky Horse Park: Visit to learn about Kentuckyโ€™s horse racing heritage and watch live competitions. ๐Ÿฅƒ Bourbon Distilleries: Take a tour of local bourbon distilleries and sample regional spirits. ๐Ÿ›๏ธ Historic Downtown: Wander through downtown Lexington for charming shops and historical landmarks. ๐Ÿฝ๏ธ Southern Cuisine: Savor hearty southern dishes like fried chicken and biscuits. ๐ŸŒณ Gardens: Explore the beautiful Ashland, The Henry Clay Estate with its gardens and trails.

Sustainable Travel

๐ŸŒพ Sustainable initiatives: Focus on supporting local farms, especially for the regionโ€™s famous bourbon distilleries and food scene. ๐Ÿ‡ Community engagement: Programs supporting local artists, entrepreneurs, and the equestrian community. ๐ŸŒฟ Conservation efforts: Protecting equestrian heritage and rural landscapes through sustainable agricultural practices. ๐Ÿž๏ธ Green spaces: More parks and trails are being developed, including the popular Legacy Trail. ๐Ÿƒ Eco-friendly transport: Expanding bike-share programs and electric vehicle stations across the city.

Lexington

TWYS: Your Ultimate Guide to Unique Travel Experiences & Insider Tips

Explore the Best Off-the-Beaten-Path Experiences:
โ€
Ready to see through a localโ€™s eyes?
Our curated guide unveils top hidden gems, secret spots, and local favorites that you wonโ€™t find in typical travel guides.
Whether itโ€™s a cozy cafรฉ tucked away in a historic neighborhood, a scenic trail only known to insiders, or unique cultural sites, has so much more to offer beyond the tourist hotspots.
Dive into our off-the-beaten-path guide and discover the true heart โ€”perfect for adventurous travelers, culture enthusiasts, and anyone looking for an authentic journey

Sign belowย for Fresh Updates

We will send you the latest curation of places and cities straight to your inbox along with access to the pop-up store & exclusive events.

Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.

Join us to stay connected. Read our updates

Unlock the Hidden Side:
โ€
Each spot in our City guide is handpicked to help you experience the city like a local, avoiding the crowds and discovering the best-kept secrets.
From charming local eateries and breathtaking viewpoints to tucked-away art galleries and vibrant local markets, this guide lets you explore beyond the surface.
Follow our recommendations for an unforgettable adventure and see why these places stand out as favorites among locals.
For more unique experiences like these, explore our full collection of off-the-beaten-path city guides and make every trip a journey of discovery.

& More Cities to Explore:

๐ŸŒ‰๐ŸŒ๐Ÿš‹
San Francisco
SF Hidden Spots Discovery
15.1ยฐC
US Dollar (USD) $
San Francisco is famous for its picturesque Golden Gate Bridge, diverse neighborhoods, and vibrant arts scene. The city has more than 200 parks, including Golden Gate Park, which is larger than New York's Central Park. Known for its cable cars and tech startups, San Francisco is a global leader in innovation and technology. Its rich history is intertwined with the California Gold Rush and the LGBT rights movement, while its stunning bay views, iconic architecture, and thriving cultural scene continue to draw visitors from around the world.
๐ŸŒ‰๐ŸŒ๐Ÿš‹
San Francisco
SF Hidden Spots Discovery
United States of America
15.1ยฐC
US Dollar (USD) $
San Francisco is famous for its picturesque Golden Gate Bridge, diverse neighborhoods, and vibrant arts scene. The city has more than 200 parks, including Golden Gate Park, which is larger than New York's Central Park. Known for its cable cars and tech startups, San Francisco is a global leader in innovation and technology. Its rich history is intertwined with the California Gold Rush and the LGBT rights movement, while its stunning bay views, iconic architecture, and thriving cultural scene continue to draw visitors from around the world.
๐Ÿฅƒ๐Ÿ‡๐ŸŽถ
Louisville
Southern Charm Louisville
United States of America
12-25ยฐC
US Dollar (USD) $
The birthplace of legendary boxer Muhammad Ali, Louisville is a city rich in history and culture. Known for its famous Kentucky Derby at Churchill Downs, Louisville is also a hub for bourbon production, with a variety of distilleries to explore. The city celebrates a unique mix of Southern charm and progressive urban development, with historic sites like the Muhammad Ali Center and the Louisville Mega Cavern. The city is also known for its thriving arts scene, bourbon heritage, and community spirit.
๐Ÿ•Œ๐Ÿœ๏ธ๐ŸŒด
Marrakech
Cultural Marrakech Vibes
Morocco
20ยฐC
Moroccan Dirham (MAD) ุฏ.ู…
Known for its one of the largest traditional souks, Marrakech offers a sensory overload with its vibrant markets, exotic spices, and colorful textiles. The city is home to stunning landmarks such as the Jardin Majorelle, the Koutoubia Mosque, and the Saadian Tombs. Marrakechโ€™s Medina, a UNESCO World Heritage Site, is a labyrinth of narrow streets filled with history, art, and culture. The city's lively atmosphere is complemented by its luxurious riads and traditional Moroccan cuisine.
๐Ÿซ๐Ÿป๐Ÿ’Ž
Brussels
Political Hub Brussels
Belgium
8ยฐC โ€“ 16ยฐC
Euro (EUR) โ‚ฌ
Manneken Pis, a small statue that has become a national symbol, is just one of the many quirky features of Brussels, Belgiumโ€™s capital city. Known for its rich history, beautiful architecture, and delicious food, Brussels is home to historic landmarks such as the Grand Place and the Atomium. It is also the de facto capital of the European Union, housing major EU institutions. Belgian cuisine, famous for waffles, fries, and chocolate, can be found around every corner of the city.
๐Ÿฐ๐ŸŽ ๐Ÿบ
Nuremburg
Medieval Charm Nuremburg
Germany
7ยฐC โ€“ 16ยฐC
Euro (EUR) โ‚ฌ
Nuremberg, one of the most historically significant cities in Germany, played a pivotal role in medieval European politics. The city is home to the Nuremberg Castle, a major landmark, and the Nuremberg Trials, which were held after World War II to prosecute war criminals. The Old Town (Altstadt) is full of medieval charm, with cobbled streets, half-timbered houses, and the beautiful St. Lorenz Church. Known for its famous Christmas market, Nuremberg is also renowned for its bratwurst, gingerbread cookies, and its role in the production of high-quality toys
๐ŸŒŠ๐ŸŽถ๐Ÿ›๏ธ
Chennai
Cultural & Coastal Chennai
India
29ยฐC
Indian Rupee (INR) โ‚น
Marina Beach in Chennai is the longest natural urban beach in India and a key attraction in this bustling South Indian city. Chennai is known for its thriving arts and music scene, with classical dance performances and concerts held regularly. The city is also famous for its rich cultural heritage, including historic temples, colonial architecture, and unique festivals like Pongal. Chennai's blend of traditional culture, modern attractions, and beautiful coastline makes it an exciting destination for both cultural exploration and beach relaxation.
๐ŸŽ๏ธ๐ŸŽฐ๐Ÿ’Ž
Monaco
Luxe & Glamorous Monaco
Monaco
16ยฐC
Euro (EUR) โ‚ฌ
Monaco, the second smallest country in the world, is renowned for its luxury lifestyle, glamorous casinos, and the world-famous Monte Carlo Casino. The countryโ€™s Mediterranean coastline and its wealth of upscale hotels, shops, and restaurants attract the rich and famous. Monaco is also famous for its prestigious Formula 1 Grand Prix race and its royal family. Visitors can explore the beautiful Prince's Palace, the Oceanographic Museum, and indulge in world-class dining and entertainment. Monaco's stunning vistas and opulent atmosphere make it a top destination for luxury seekers.
๐Ÿ›ฅ๏ธ๐Ÿ–๏ธ๐ŸŒธ
Portofino
Scenic & Serene Portofino
Italy
16-27ยฐC
Euro (EUR) โ‚ฌ
Ephesus, an ancient Roman harbor city, is a major historical site in Turkey, known for its impressive ruins, including the Temple of Artemis, one of the Seven Wonders of the Ancient World. The cityโ€™s extensive archaeological remains include the Great Theater, Celsus Library, and a network of ancient roads. Ephesus offers visitors a glimpse into the grandeur of the Roman Empire, with its remarkable structures and rich history. Its proximity to the Aegean coast also adds scenic beauty to this historical gem.
๐ŸŒŠ๐ŸŽถ๐Ÿ›๏ธ
Chennai
Cultural & Coastal Chennai
India
29ยฐC
Indian Rupee (INR) โ‚น
Marina Beach in Chennai is the longest natural urban beach in India and a key attraction in this bustling South Indian city. Chennai is known for its thriving arts and music scene, with classical dance performances and concerts held regularly. The city is also famous for its rich cultural heritage, including historic temples, colonial architecture, and unique festivals like Pongal. Chennai's blend of traditional culture, modern attractions, and beautiful coastline makes it an exciting destination for both cultural exploration and beach relaxation.