When winter rolls in and Lexington’s temperatures dip, it’s the perfect time to embrace cozy indoor activities. From historical sites and art galleries to local distilleries and culinary hotspots, there’s plenty to see and do in Lexington without braving the chilly outdoors. Here’s a weekend itinerary to help you make the most of Lexington’s indoor attractions for a memorable, warm, and welcoming winter escape.
Day 1: Explore Local History and Culture
Morning: Start at the Aviation Museum of Kentucky
Begin your day at the Aviation Museum of Kentucky, located near the Blue Grass Airport. This museum is a hidden gem, showcasing Kentucky’s rich aviation history with vintage aircraft, military jets, and interactive exhibits. It’s perfect for a family-friendly outing or for anyone interested in the mechanics of flight.
Location: 4029 Airport Rd, Lexington, KY
Tip: Check out the flight simulator for a hands-on experience that lets you feel like a real pilot.
Late Morning: Tour the Mary Todd Lincoln House
Step back in time with a visit to the Mary Todd Lincoln House, the childhood home of the First Lady and a fascinating look into 19th-century life in Kentucky. The house is beautifully preserved, with original furnishings and memorabilia that bring Mary Todd Lincoln’s story to life. It’s an intimate, indoor experience that history buffs will especially enjoy.
Location: 578 W Main St, Lexington, KY
Tip: Be sure to ask the guides about the Todd family’s history and connections in the area.
Afternoon: Lunch at Josie’s
Warm up with a hearty lunch at Josie’s Restaurant, a beloved local spot known for its comforting dishes and welcoming vibe. Enjoy Southern classics like fried chicken and biscuits or their famous sweet potato pancakes if you’re in the mood for brunch fare.
Location: 821 Chevy Chase Pl, Lexington, KY
Tip: Josie’s can get busy on weekends, so consider going a bit early to secure a table.
Afternoon: Discover Art at the Lexington Art League
Spend the afternoon exploring the Lexington Art League at the historic Loudoun House, where you’ll find rotating exhibitions of contemporary art by Kentucky artists. The art league’s beautiful galleries and diverse artwork make for an inspiring visit, even on the coldest days.
Location: 209 Castlewood Dr, Lexington, KY
Tip: Check their event schedule—January often features local artist showcases and special exhibits.
Evening: Dine at OBC Kitchen
Wrap up the day with dinner at OBC Kitchen, an inviting restaurant that offers elevated Southern dishes and an impressive bourbon selection. Known for its cozy vibe and creative cocktails, OBC Kitchen is a favorite for both locals and visitors.
Location: 3373 Tates Creek Rd, Lexington, KY
Tip: Don’t miss their “Bacon in a Glass” appetizer—a delicious start to a memorable meal.
Day 2: Lexington’s Distilleries, Coffee Culture, and Unique Finds
Morning: Coffee and Pastries at Third Street Stuff & Coffee
Kick off the day with a warm cup of coffee at Third Street Stuff & Coffee, a funky, colorful café with an eclectic vibe. Known for its artisan lattes and fresh pastries, Third Street is a cozy spot to fuel up for a day of indoor exploring.
Location: 257 N Limestone, Lexington, KY
Tip: Take a moment to enjoy the café’s unique, art-filled interior—it’s a local favorite for good reason!
Late Morning: Visit the International Museum of the Horse
Located within the Kentucky Horse Park, the International Museum of the Horse offers a fascinating look at Kentucky’s equestrian heritage. Spend a few hours exploring exhibits that highlight the history and global impact of the horse industry, from ancient civilizations to modern Thoroughbred racing.
Location: 4089 Iron Works Pkwy, Lexington, KY
Tip: Even if it’s winter, some exhibits provide views of the park’s scenic grounds—perfect for a peaceful moment.
Afternoon: Lunch and Tasting at West Sixth Brewing
Head to West Sixth Brewing for a relaxed lunch paired with local craft brews. This brewery offers a laid-back atmosphere, a rotating menu of seasonal beers, and delicious pub food. It’s an ideal spot to enjoy some local flavors while staying warm indoors.
Location: 501 W Sixth St #100, Lexington, KY
Tip: Try their signature beers or ask about limited releases—there’s always something new to sample!
Afternoon: Bourbon Tasting at Bluegrass Tavern
No trip to Lexington is complete without experiencing the city’s renowned bourbon culture. Bluegrass Tavern, located downtown, boasts over 400 bourbons and offers tastings in a warm, rustic setting. Spend a cozy afternoon sampling Kentucky’s best bourbons and learning about the state’s storied bourbon heritage.
Location: 115 Cheapside, Lexington, KY
Tip: If you’re new to bourbon, ask the staff for recommendations—they’re always happy to share their knowledge.
Evening: Dinner at Distilled on Jefferson
For your final evening, treat yourself to dinner at Distilled on Jefferson. Known for its innovative Southern cuisine and commitment to using fresh, local ingredients, this upscale restaurant is the perfect place to indulge in a memorable meal. The cozy, modern ambiance makes it ideal for a winter evening out.
Location: 157 Jefferson St, Lexington, KY
Tip: Be sure to make a reservation in advance, as this popular spot tends to fill up quickly.
A Cozy Winter Weekend in Lexington
Lexington offers a diverse array of indoor attractions that make winter travel both exciting and comfortable. With a blend of historical sites, art, bourbon, and delicious food, this itinerary is designed to give you a taste of everything Lexington has to offer without spending too much time in the cold. Whether you’re exploring its art galleries, savoring Kentucky flavors, or discovering its rich history, Lexington is the perfect place for a cozy winter getaway.