My fiancee and I love a good road trip and have taken quite a few over the years that have us driving up and down I-81 in Virginia (and of course making plenty of stops along the way). Below, I’ve compiled some of our favorite spots we have stopped for snacks, coffee, a bite to eat, and stretch our legs while walking through a charming downtown. I’ve listed everywhere out in order of the town you drive through when heading south on I-81 through VA.
Winchester
- Bro Bears Coffee – this drive-through coffee shop is located in a parking lot and has tons of coffee beverages to fuel you up for the first (or final) leg of your trip
- Hopscotch Coffee and Records – I love a coffee roaster that knows what they are doing and this spot fits the bill. Plus there’s a great vibe in here if you need to decompress for a bit before continuing your drive.
- Winchester Brew Works – nestled just off Old Town’s pedestrian streets—its vibrant Shenandoah Valley mural, retro arcade games, and ever‑rotating flight of house‑made brews make it the perfect pit stop on your I‑81 Virginia adventure
- Doppio Bunny – locally roasted espresso, house‑made syrups, scratch‑baked treats, and comfy vintage vibes make for a relaxing road trip stop
- Taqueria Guadalajara – casual spot for authentic Mexican food
Woodstock
- Woodstock Brewhouse – casual hangout with beers, good food, and plenty of outdoor space
- Woodstock Cafe – fresh-brewed coffee, creative sandwiches, and house-made pastas, it’s the kind of place that turns a quick break into a memorable meal
- Katie’s Custard – creamy ice cream in a cute roadside stand
New Market
Peep’s Frozen Custard – another roadside stand that makes great ice cream
Harrisonburg
- Little Grill Collective – A vegan/vegetarian friendly worker owned spot in Harrisonburg, VA. Plenty of breakfast and lunch options and the few times we’ve visited I’ve ordered the breakfast burrito – it’s so good!
- Magpie Diner – a modern corner diner with seriously excellent food and pastries. Great for grabbing a bite to eat.
Staunton
So we have actually stopped here for the night and had a seriously wonderful time so it’s always a must for us when in the area.
- Redbeard Brewing Co. – This was our favorite stop for beers in the area
- The Split Banana – Super cozy ice cream shop
- The Shack – They offer a 5 course tasting menu that’s regularly changing and was seriously one of the best meals we’ve had
- Reunion Bakery + Espresso – amazing coffee, flaky pastries, this place has it all. Don’t miss the cruffin
- Cocoa Mill – this chocolatier has something for everyone and we definitely grabbed some truffles for the road
- Crucible Coffee – if you’re looking for a really good cup of coffee, this roaster is a great stop. Make sure to grab a bag to bring home too!
Lexington
- Devil’s Backbone Outpost – One of two Devil’s Backbone locations. Great food, awesome beers, and a lovely view of mountains off the patio.
- Heliotrope Brewing – You have to try the pizza!
Buchanan
- Drip – This no frills coffee joint is perfect for fueling up. If you need to stretch your legs, check out the Buchanan swinging bridge just across the street.
Roanoke
- Sweet Donkey Coffee – In an old home, this coffee shop is serving some fun flavor combinations and I wanted to try them all. The spicy honey latte was excellent.
Bristol
- Blackbird Bakery – A true old fashioned bakery – the doughnuts really hit the spot.
- Pal’s Sudden Service – This fast food chain lured me in with its seriously adorable building and I can’t resist an order of french fries!






















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