One of the oldest general stores in Vermont, with a Cadillac Cooker smoker in the parking lot. Maple syrup breakfast sandwiches sell out by 9am. Smoked brisket and pork, cider donuts fried fresh three times a week, house-made chocolates.
📍 4934 VT Route 22A, Addison, VT
🕐 Mon–Sat 6am–6pm | Closed Sunday
A 140-year-old general store that is also Ripton's post office. Woodstove in the back, hand-cranked cash register, antique postal boxes on the wall, penny candy, old-fashioned soda fountain. The real thing.
📍 Route 125 at Lincoln Road, Ripton, VT
🕐 Open daily
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The natural stop at the end of the Middlebury Gap drive — at the junction of Routes 125 and 100 in tiny Hancock. Made-to-order sandwiches, pizza, homemade baked goods, local root beer on tap.
📍 38 VT Route 125, Hancock, VT
🕐 Open 7 days, 10am–6pm
A genuine Vermont crossroads store at the junction of the hill towns. Gas, hot food, beer, groceries. The roads in from every direction are beautiful.
📍 1858 VT Route 17, Bristol/Starksboro, VT
🕐 Mon–Fri 7am–7pm | Sat–Sun hours vary
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The beating heart of Huntington, run by Linda Pecor for over 43 years. Gas, groceries, deli sandwiches, exceptional craft beer selection, regular brewery tastings. The stop before or after Camel's Hump.
📍 2177 Main Road, Huntington, VT
🕐 Open daily 9am–6pm
Kim Jewell started barbecuing for neighbors until her family bought her a food truck. Now it's a seasonal institution down a dirt road in Monkton. Hand-cut fries, grass-fed burgers, creemees. Worth finding.
📍 1915 Hardscrabble Road, Monkton, VT
🕐 Seasonal ~May–Oct | Check Facebook for hours
Authentic Indian cooking down Bakery Lane off the Middlebury waterfall — garlic naan from a clay tandoor oven, views of the Battell Bridge. Hard to find the first time; easy to come back to.
📍 1 Bakery Lane, Middlebury, VT
🕐 Tue–Sat 11:30am–2pm & 4:30–9pm | Sun 11:30am–2pm & 4:30–8:30pm | Closed Mon
Organic, vegan, made-to-order juices, smoothies, acai bowls, soups, and salads on Merchants Row. Everything fresh, local where possible. Started in a kitchen in 2015.
📍 16 Merchants Row, Middlebury, VT
🕐 Mon–Fri 9am–4pm | Sat 9am–3pm | Sun 10am–3pm
The Roast Beef Kicker — medium-rare beef, Vermont cheddar, horseradish mayo on a grilled roll — is the reason to go. Breakfast sandwiches, excellent fries. Family-owned.
📍 1396 Route 7 South, Middlebury, VT
🕐 Mon–Sat 7am–3pm | Sun 8am–2pm
Downtown Middlebury's anchor bakery since 1986. Almond croissants, sourdough baked in-house, the Vermonter sandwich (goat cheese, watercress, honey mustard), and an outdoor deck overlooking the creek.
📍 14 College Street, Middlebury, VT
🕐 Mon–Sat 7am–4pm | Sun 8am–2pm
Middlebury's neighborhood meat market and deli, back after a gap in service. Custom-butchered meats, house-made sausages, great deli sandwiches, fresh local produce.
📍 3 Elm Street, Middlebury, VT
🕐 Mon–Sat from 6am (hours vary — call ahead)
A working roastery and café in the historic Battell Block, under original tin ceilings. Single-origin beans, seasonal sourcing, open every day. The maple latte earns every good review it gets.
📍 24 Merchants Row, Middlebury, VT
🕐 Daily 8am–4pm
Italian deli in the Marble Works — house-made mozzarella, cannoli, store-made gelato, fresh seafood delivered daily, the Soprano sandwich (prosciutto, fresh mozzarella on housemade bread). Eat at the picnic tables overlooking the Otter Creek falls.
📍 99 Maple Street, Suite 13A, Marble Works District, Middlebury, VT
🕐 Wed–Fri 10am–6pm | Sat 10am–5pm | Closed Sun–Tue
Family-owned sushi and Asian grocery that opened in 2025. Chef Aung Oo brings 10+ years of experience. Fresh rolls, nigiri, platters, plus kimchi, dumplings, and a real Asian grocery selection.
📍 21 MacIntyre Lane, Middlebury, VT
🕐 Mon–Sat 10am–7pm
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Looks modest, eats well. Generous portions, honest cooking, free self-serve hot tea. The vegetable mei fun is excellent. A reliable local staple that consistently overdelivers.
📍 20½ Seymour Street, Middlebury, VT
🕐 Mon–Wed 4–8:30pm | Thu closed | Fri–Sat 4–9pm | Sun closed
A Middlebury family pizza and pasta institution since 1982. Curbside takeout only now — pizza, pasta, subs, calzones, salads, wings. Pasta trays for big groups. Co-op members get 10% off.
📍 10 Washington Street, Middlebury, VT
🕐 Mon, Wed–Sun 10am–7pm | Closed Tuesday
New York-style and Sicilian slices always hot in the case. Open kitchen — you can watch everything from dough to oven. Creative specialty pies, take-and-bake options, weekday lunch specials.
📍 21 MacIntyre Lane, Middlebury, VT
🕐 Mon–Fri 11am–8pm | Sat 1–8pm | Closed Sunday
Wood-fired flatbreads in the historic Marble Works, overlooking Otter Creek falls. The Punctuated Equilibrium is the classic. Best bar in the area. Weekly Benefit Bake nights support local nonprofits.
📍 137 Maple Street, Suite 29F, Marble Works, Middlebury, VT
🕐 Tue 5–9pm | Wed–Thu 11am–2pm & 5–9pm | Fri–Sat 11am–2pm & 4:30–9pm | Closed Sun & Mon
Community-owned grocery store since 1976. Local and organic throughout, excellent deli and prepared foods. Anyone can shop; membership pays off quickly if you're local.
📍 9 Washington Street, Middlebury, VT
🕐 Daily 8am–7pm
Bristol's pizza institution. The Junebug Pie — pesto, spinach, feta, sausage, artichoke, portobello — is a local legend. House dressing has its own following. Exactly what a neighborhood pizza place should be.
📍 8 Main Street, Bristol, VT
🕐 Tue–Sat 11am–8pm | Closed Sun & Mon
Bristol's all-day diner on Main Street. The venison burger — Vermont Smoke & Cure bacon, Cabot cheddar, Switchback caramelized onions on a pretzel bun — is the signature. Good breakfast, full bar, tin ceiling.
📍 24 Main Street, Bristol, VT
🕐 Mon–Sat breakfast through dinner | Sunday brunch | Full bar
At the crossroads of Routes 100 and 125 in the heart of the Green Mountains, the Old Hancock Hotel has been a stop for travelers since 1788. Today it operates as the Heart of Hancock — fresh American home cooking, daily baked goods, maple shakes, and porch-side live music on weekends in summer. The meatloaf has its own following, the apple pie is made in-house, and the porch is the right place to sit after Texas Falls or the Middlebury Gap drive. Seasonal, so check before you go.
📍 3 VT Route 125, Hancock, VT (junction of Rt. 100 & Rt. 125)
🕐 Seasonal (May–fall) | Mon–Tue & Thu–Sat 10am–6pm | Sun 9am–6pm | Closed Wed | Check Facebook for current status
Built in 1810 as a stagecoach stop at the foot of the Middlebury Gap, the Waybury is one of Vermont's oldest continuously operating inns — and since 2024, under the stewardship of three East Middlebury natives including chef Tony Petri, who grew up next door and trained in kitchens in Philadelphia, New York, and New Orleans before coming home to run it. Two menus: a tavern side with the famous shepherd's pie and a burger worth the drive, and a fine dining side with dishes like Moroccan-spiced rack of lamb and vegetarian Wellington. Weekend brunch is open to the public. If you recognize the building from the 1980s sitcom Newhart, you're not wrong — the exterior stood in for the fictional Stratford Inn for eight seasons.
📍 457 East Main Street (Route 125), East Middlebury, VT
🕐 Mon & Thu–Fri 4–8pm | Sat–Sun 7:30–11:30am & dinner | Closed Tue–Wed | First Sunday of the month: brunch buffet 10am–1pm
A year-round Saturday market with 50+ vendors at the VFW Hall on Exchange Street — outdoors May through October, indoors November through April. Strong in organic vegetables, local meats and eggs, and Addison County cheeses. Nearly two-thirds of vendors sell agricultural products direct from their farms. SNAP/EBT, Farm to Family, and Crop Cash accepted. A reliable weekly fixture worth building a Saturday morning habit around.
📍 530 Exchange Street (VFW Hall), Middlebury, VT
🕐 Saturdays 9am–12:30pm year-round | Free
Bristol's weekly summer market on the town green — local produce, crafts, and live music on Monday evenings. Smaller and more community-feel than the Middlebury market, and a good excuse to walk through town after. Pairs naturally with dinner at Cubbers or a drink somewhere along Main Street.
📍 Bristol Town Green, Bristol, VT
🕐 Mondays 4–7pm, summer season | Free
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Dr. Ana Guigui plays a Steinway Model B grand in the historic ballroom — Broadway-caliber piano Friday and Saturday nights, no cover. Singalong and unplugged karaoke from 8pm.
📍 20 Park Street, Brandon, VT
🕐 Fri & Sat 7–9:30pm | Pub: Thu–Tue 5–9pm
The best open mic in the area. Walk-up format, genuine talent, welcoming to beginners. Order pizza from BHOP next door and eat it at your table. Every Thursday.
📍 43 Center Street, Brandon, VT
🕐 Open mic Thu 6–8:30pm | Thu 4–8pm | Fri 4–9pm | Sat 12–7pm | Sun 12–5pm
Fifth-generation 960-acre Monkton farm with a store open seven days a week. Beef, pork, turkey, chicken, eggs, maple syrup, alpaca yarn, felted goods. Visitors always welcome.
📍 Monkton Road, Monkton, VT
🕐 Open 7 days — call ahead to confirm
A pub and restaurant sitting right on the south end of Lake Dunmore, inside the Waterhouses marina complex — one of the few places in Addison County where you can eat dinner with your feet practically in the water. Deck seating overlooking the lake and the mountains. Burgers, flatbreads, tacos, wings, salads, craft beer on tap. Arrive by car or by boat. Seasonal — check Facebook or the website for current hours before making the drive.
📍 937 W Shore Road, Salisbury, VT
🕐 Wed–Sat 4:00pm–9:00pm | Closed Sun–Tue | Seasonal
Open since 1951, on Route 22A roughly halfway between Bridport and Shoreham. Counter with stools, booths, Formica, historic photos on the walls — the real thing, essentially unchanged. Breakfast all day, fried chicken, hot roast beef sandwich, homemade pies. Open seven days starting at 5am. If you're driving the 22A corridor, this is the stop.
📍 450 VT Route 22A, Shoreham, VT
🕐 Mon–Thu 5:00am–8:00pm | Fri–Sun hours vary | Open 7 days