Itinerary

A Long Winter Weekend in LYH

Itinerary Overview

Spend a winter weekend in Lynchburg exploring unique hotels, charming downtown streets, local shops, and indoor fun. Enjoy cozy stays along the James River, stroll art-filled streets, browse the Community Market, and warm up with delicious meals and rooftop views. Perfect for families, friends, or anyone looking for a winter escape.


3 Days
Daily Breakdown
1
Friday: Welcome to LYH!
Hotel Check-In
❄️ Warm Welcome

Kick off your long weekend by checking into one of Lynchburg’s standout places to stay—each offering a memorable way to settle in before heading out to explore the City!

  • Craddock Terry Hotel – Once a turn-of-the-century shoe factory, this boutique hotel blends historic brick and riverfront charm with modern comfort. Located in downtown Lynchburg, it is just steps from trails, shops, and dining. Comfortable rooms and thoughtful touches, including a friendly hotel dog named Penny Loafer, make it a cozy base for a winter getaway.
  • The Virginian Hotel – A downtown landmark blending historic charm with modern comfort. Polished rooms, on-site dining, and a rooftop lounge with city views make it a convenient stay for exploring downtown shops, galleries, and entertainment.
  • Silo on the James – This converted grain silo along the James River offers a unique and cozy stay just minutes from downtown. Warm up by the indoor fireplace or bundle up and enjoy the fire pit and river views.
  • James Station – A renovated train caboose with modern comforts, a kitchenette, cozy beds, and a deck with hammock and fire pit. A whimsical, memorable option for families or anyone who loves a unique getaway.
Afternoon
🚶‍♂️ Stroll & Museum

After checking into your hotel, head out for a relaxed walk through downtown Lynchburg. If the weather cooperates, bundle up and make your way along the Bluffwalk, where river views and historic architecture set the tone for the weekend.

Climb Monument Terrace, a local landmark and scenic staircase that connects downtown to the Court Street area. At the top, you’ll arrive at the Lynchburg Museum and Visitor Center, a perfect stop to warm up, learn about the city’s history, and get oriented before dinner.

From there, it’s an easy walk back to nearby restaurants for dinner and drinks.

Dinner
🍽️ Downtown Eats

After your downtown stroll and museum stop, settle in for an evening of great food, drinks, and city views. Whether you’re craving Italian comfort food, refined dining, or a casual riverside meal, downtown Lynchburg has plenty of cozy options for a winter night out.

  • Fratelli – A warm and welcoming Italian eatery serving pizza, pasta, and classic dishes. Perfect for a laid-back dinner with a glass of wine in the heart of downtown.
  • Shoemakers American Grille – Located at the Craddock Terry Hotel, Shoemakers pairs historic character with fine dining. Exposed brick and wood beams frame a menu of steaks, fresh seafood, and thoughtfully curated cocktails.
  • Dish – Creative, shareable plates and globally inspired flavors make Dish a downtown favorite. Enjoy tapas, entrées, and attentive service in a relaxed setting.
Evening
🥂 Drinks & Live Music

After dinner, head out for drinks and take in downtown Lynchburg from a cozy rooftop or lively lounge. Whether you’re in the mood for skyline views, a curated wine selection, or live music, these spots offer the perfect way to extend your evening.

  • No. 7 Rooftop Bar – Located just above the Bluffwalk, this rooftop bar offers sweeping views of downtown, a relaxed atmosphere, and fire pits ideal for cocktails or a wine flight before or after dinner.
  • Skyline Grill at The Virginian Hotel – Downtown’s rooftop dining spot with city views from inside or on the patio. Fire pits, cocktails, wine, and elevated American fare make it a perfect place to watch the sunset over the James River.
  • Reserve Tasting Room & Lounge – A cozy wine lounge in downtown Lynchburg with a curated selection of Virginia and regional wines, flights, and charcuterie boards. Relax indoors or outside under the covered patio and enjoy a sophisticated yet relaxed atmosphere with occasional live music.
  • Raven Lounge – Lynchburg’s premier wine and charcuterie bar with an inviting lounge vibe. Sip wine cocktails, wine slushies, mocktails, mimosas, beers, and more while enjoying live music and stylish, laid-back nightlife in the heart of downtown.
2
Saturday: A Full Day in LYH
Morning
☕ Coffee & Treats

Start your Saturday slow with a warm drink and a sweet bite before exploring the day ahead.

  • The Loving Co. – A cozy coffee shop and retail space offering lattes, tea, books, and local handmade goods. This family-owned spot makes it easy to feel right at home while enjoying a morning pick-me-up.
  • Father’s Cafe & Bakery – Handcrafted breads, fresh pastries, and classic donuts made with care from the finest ingredients. A perfect indulgence to kick off your winter morning.
  • Batter Bar – A bake shop and coffeehouse specializing in sweet and savory crepes, plus other pastries. Grab a crepe or pastry to enjoy while planning your next stop, whether downtown or outdoors.
Afternoon
🎮 Active Indoor Fun

Spend a lively winter day indoors enjoying movement, games, and local flavor. Perfect for families, friends, or anyone looking to burn off energy while staying warm.

  • Super Rad Arcade – A retro-inspired arcade packed with classic games for all ages. Challenge the kids to a friendly competition or relive your own favorites in a high-energy indoor setting with a fun, nostalgic atmosphere.
  • Rise Up Climbing – Test your strength and agility at this indoor climbing gym. With walls, boulders, and obstacle courses for all skill levels, Rise Up is a great way to stay active while having fun in a safe, climate-controlled space.
  • LaHaye Ice Center – Lace up your skates for a spin around the full-size rink, home to Liberty University hockey. Enjoy public skating sessions or catch a game while soaking up the lively winter vibe. Don’t forget your tall socks!
  • Liberty Mountain Snowflex Centre – Try a winter sport twist indoors with this snow-sport center. Beginners and seasoned snow-lovers alike can enjoy skiing, snowboarding, or tubing on artificial snow, offering a unique and playful way to embrace the season without venturing outdoors.
Lunchtime
🍴 Local Lunch

Pause mid-day to recharge with a light lunch. Local favorites offer sandwiches, salads, soups, and shareable plates—perfect for fueling up before the afternoon adventures.

  • Farm Basket – Light, fresh, and local. Choose from combos like soup & half sandwich, salad sampler, or boxed lunch. While you’re there, browse Virginia-made goods in their shop.
  • Magnolia Foods – Casual lunch spot with sandwiches, salads, and desserts, plus wine, beer, cheese, and specialty gifts. Perfect for a quick bite or a take-out picnic.
  • Iron & Ale – Another great option for a relaxed, flavorful lunch featuring local ingredients and hearty options to keep you fueled for the afternoon

Afternoon Break

After a morning of coffee, pastries, and exploring, spend some time recharging and freshening up at your hotel before heading out for the evening. The afternoon is yours to relax, plan your own dinner, and enjoy a little downtime.

Evening
🎭 Saturday Show

When you’re ready, enjoy dinner at a spot of your choice downtown or nearby, then cap the night with a show at one of Lynchburg’s theaters. Winter evenings in the city offer the perfect mix of cozy ambiance and entertainment.

  • Academy Center of the Arts Historic Theatre – One of Lynchburg’s most treasured performance venues, this beautifully restored historic theater originally opened in 1905 and welcomes nationally acclaimed artists. Recent acts have included the Bacon Brothers, Charlottesville Ballet: A FairyTale Gathering, and Tusk, a classic Fleetwood Mac tribute.
  • Wolf Den (Wolfbane Productions) – A dynamic arts organization presenting innovative theatrical productions in downtown Lynchburg. Known for accessible, high-quality performances such as their adaptations of Dracula and A Christmas Carol, Wolfbane creates immersive experiences that captivate audiences.
  • Commerce Street Theater – A community theater dedicated to engaging, inclusive programming in an intimate black-box space in downtown Lynchburg. Offering a variety of plays and theatrical performances throughout the year, this venue brings local creativity to life on stage.
3
Sunday: Stories of the City
Morning
☕Slow Morning & Cozy Coffee

Ease into a Sunday in Lynchburg with a slow, cozy morning. Treat yourself to a warm drink, fresh pastries, or a hearty breakfast at one of the city’s favorite morning spots. Start the day relaxed, plan your sightseeing, and fuel up for a day of history and exploration.

  • Bacon St. Bagels – Freshly baked bagels and coffee to kickstart your morning. Perfect for grabbing a quick bite or lingering over a hot drink.
  • The Flour District – A bakery and café serving pastries, breakfast plates, and locally roasted coffee. Its inviting atmosphere makes it easy to start the day slow.
  • My Dog Duke’s Diner – Classic breakfast fare, specialty coffee, and comfort favorites in a beautifully restored downtown building. 
Afternoon
🏛️ Explore LYH History

After breakfast, spend the day exploring some of Lynchburg’s historic and cultural sites. Many are open on Sundays, making it easy to plan a relaxed day.

  • Point of Honor – Explore this historic hilltop fort and mansion with panoramic views of Lynchburg and the James River. Walk the grounds, admire the architecture, and take in the city from above. Bundle up and enjoy a scenic winter stroll along the trails.
  • Maier Museum of Art – Experience fine art and rotating exhibits that highlight both regional and national artists. A peaceful spot to wander indoors on a winter Sunday.
  • Thomas Jefferson’s Poplar Forest – Tour the historic home and beautifully landscaped grounds of Jefferson’s private retreat. Walk the gravel paths, admire the architecture, and stop by the gift shop for a unique keepsake.
  • Old City Cemetery – One of Lynchburg’s oldest historic sites. Stroll among the 27 acres of monuments, learn about the city’s past, and enjoy a quiet outdoor walk.
Evening
🥪 Sunday Eats

After a day of history and sightseeing, Sunday evening is yours to unwind. Whether you want to relax at your hotel, take a stroll if the weather cooperates, or check out a new favorite spot for dinner and drinks, the choice is yours.

Here are some unique Lynchburg favorites to consider:

  • The World Famous Stadium Inn – Located across from the Lynchburg City Stadium Complex, this iconic bar and restaurant offers a welcoming, lively atmosphere. Enjoy craft beer, wine, and hearty food while soaking in a classic Lynchburg vibe.
  • Rivermont Pizza – Located on historic Rivermont Avenue, Rivermont Pizza serves specialty pizzas, salads, and appetizers with local ingredients in a casual environment. 
  • Cavalier Store – A one-of-a-kind Lynchburg tradition. Once a carriage house and trolley turnaround, now a spot for burgers, seasoned fries, and classic comfort food. Dine in or take out while checking out the eclectic license plates lining the walls. Cash only, but ATM is available.
4
Monday: Until Next Time!
Check-Out
👋 Stretch & Say Goodbye

Before heading home, take a final moment to enjoy Lynchburg’s natural beauty. If the weather cooperates, get moving with a stroll or bike ride along Blackwater Creek Trail, one of the city’s most scenic outdoor spaces.

Make a stop at Percival’s Island to check out the LOVE Sculpture, a peaceful way to cap off your long weekend.

After your walk, it’s time to check out and start your journey home — with memories of a cozy, activity-packed Lynchburg winter getaway.