Whether it’s fine dining railside, a casual cafe lunch, conversation over a coffee cup or pint glass, or provisions from the local butcher to grill at home, Ashland offers eats and drinks to satisfy all tastebuds.
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
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
Enjoy flavorful Mexican-American dishes in a warm, family-friendly setting. Locals rave about the signature margaritas and sangria!
📍428 England Street, Ashland, VA 23005
📞 804-496-6796
🌐 Visit Site
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
A beloved Ashland lunch spot known for fresh fare, boxed lunches, catering, gift baskets, homemade breads, and bakery treats—made from scratch with love.
📍102 N Railroad Avenue, Ashland, VA 23005
📞 804-798-8331
🌐 homemadesbysuzanne.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
Restaurant featuring Southern Comfortable food, drinks, and atmosphere. Specializing in barbecue, brisket and smoked chicken freshly prepared on premises. Private parties and special event catering available.
511 Thompson St
Ashland, VA 23005
(804) 798-3287
jakesplaceashland.com
Origin is a sister company of Center of the Universe Brewing Company. Built for research, development, and teaching of all things beer.
106 S Railroad Ave
Ashland, VA 23005
(804) 299-2389
originbeerlab.com
A family-friendly sports bar in the heart of Ashland serving up classic American favorites—from burgers to wings—with plenty of TVs to catch every game.
📍504 England Street, Ashland, VA 23005
📞 804-496-6700
🌐 https://iloveashlandva.com/us/ashland/-/ashland-feed-store/
Sugar Fix Bakery offers a variety of custom decorated sugar cookies and baked goodies. Custom orders available.
105-B England Street
Ashland, Virginia
804-368-7718
sugarfixbakery.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/
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
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
Treat yourself to their mouthwatering fresh, warm tortillas, delightful international candies, and heavenly pastries. Make every day a party when you stock up on groceries, colorful piñatas and festive party supplies!
Don’t miss their highly acclaimed food truck, serving authentic Mexican dishes that will transport your taste buds straight to the heart of Mexico.
109A S Washington Hwy
Ashland, VA 23005
(804) 299-3667
Dream big, eat well. Today's goals start with a tasty breakfast. Open daily from 8 AM - 2 PM.
100 N Railroad Ave,
Ashland, VA 23005
(804) 368-8671
A hometown favorite since 1968. Enjoy hearty meals, a friendly bar, billiards, and dancing—plus patio seating when the weather’s just right.
📍412 England Street, Ashland, VA 23005
📞 804-752-2990
🌐 https://iloveashlandva.com/us/ashland/-/andys-restaurant/