A staple in Downtown Ashland, Ashland Meat Company offers farm-to-table provisions, regional meats, deli platters, and gourmet groceries. Whether you're planning a picnic or stocking your pantry with local flavors, this specialty grocer brings high-quality, fresh food to the heart of town.

📍107 S Railroad Avenue, Ashland, VA 23005
📞 804-798-8311
🌐 ashlandmeatco.com

Ashland Museum tells the story of our town through words, images, voices, and objects. Plus, tour the fully restored 1926 C&O red caboose for a trip back in time to the heyday of the railroad. Groups are welcome, call to make arrangements.

Ashland Museum
105 Hanover Avenue
(804) 368-7314
ashlandmuseum.org

Savor authentic Thai cuisine made fresh to order. Ban Thai offers homestyle favorites, bold flavors, and convenient takeout and delivery options.

📍124-B Thompson Street, Ashland, VA 23005
📞 804-299-3644
🌐 Vist site

Located along the railroad tracks, The Caboose features farm-to-table dining, a curated wine and craft beer selection, and local artisanal goods. A go-to spot for lunch, coffee, or gathering with friends in Downtown Ashland.

📍108 S Railroad Ave, Ashland, VA 23005
📞 804-798-2933
🌐 cabooseashland.com

Step into the warmth, charm, and hospitality of The Henry Clay Inn — a Georgian-style Inn located right in the heart of historic downtown Ashland. Weddings, meetings, and private events hosted on the premises. Dining room serves full menu Thursday through Monday.

114 N. Railroad Ave
Ashland, Virginia
(804) 798-3100
henryclayinn.com

With 50 TVs, pool tables, live music on weekends, and a menu full of all-American favorites, Huddle Up is your go-to game day (or any day) hangout spot.

📍407 England Street, Ashland, VA 23005
📞 804-798-5979
🌐 huddleupsportsbar.com

A local icon serving upscale Southern cuisine with a front-row view of the railroad. This two-story landmark offers unforgettable meals, historic charm, and live train views.

📍100 S Railroad Avenue, Ashland, VA 23005
📞 804-752-6410
🌐 ironhorserestaurant.com

Create your own dessert adventure with frozen yogurt, gelato, sorbets, frozen drinks, and all the toppings your sweet tooth can handle—right in downtown Ashland.

📍210 England Street, Ashland, VA 23005
📞 804-496-6915
🌐 https://iloveashlandva.com/us/ashland/-/sweet-frog/

A flexible, modern event space in the heart of Ashland—perfect for receptions, workshops, dance classes, and private gatherings.

📍110 Thompson Street, Ashland, VA 23005
📞 804-412-8591
🌐 Visit site

Explore a wonderland of toys and model trains at this one-of-a-kind shop in Ashland’s historic downtown. Perfect for curious kids and collectors of all ages.

📍104 S Railroad Avenue, Ashland, VA 23005
📞 804-368-0063
🌐 trainandtoystore.com

Posh antiques and collectibles shop. Open Saturdays only.

112C Thompson Street
Ashland, VA 23005

Bold, beautiful ink from a rotating crew of talented tattoo and PMU artists. Walk-ins welcome, or book your next statement piece today.

📍113 S Railroad Avenue, Ashland, VA 23005
🌐 Visit site

Delicious Italian dishes made from scratch—think gourmet pizzas, hearty pastas, steaks, and seafood. A family favorite with full bar service.

📍435 England Street, Ashland, VA 23005
📞 804-368-7204
🌐 Visit site

The "Secretariat Racing Into History" monument, sculpted by acclaimed artist Jocelyn Russell, stands as a remarkable tribute to the legendary Triple Crown champion in Virginia.

At the corner of England Street and Railroad Avenue on Randolph-Macon College

Ashland’s tribute to trains includes a massive mural depicting a locomotive that traveled Ashland’s tracks 50 years ago.

108 S Railroad Ave, Ashland, VA

Family-friendly dining meets stone-fired flavor! Enjoy artisan pizzas, sandwiches, and fun cocktails in a cozy downtown setting.

📍107 S Railroad Avenue, Ashland, VA 23005
📞 804-800-9096
🌐 Visit site

Classic coffee, tea, books, and their shots rock!

112 Thompson St
Ashland, VA 23005
(804) 847-8747