Vermont's largest agricultural fair — five days in early August. Demo derby, truck and tractor pulls, livestock shows, midway rides, live music every night. All the agricultural Vermont you can absorb in a week.
📍 1790 Field Days Road, New Haven, VT
🕐 Annual, first week of August | Admission $15–$20 | Free parking
A full week of free live music every July on the Middlebury Village Green — Vermont's best free performance series. Noon family shows weekdays, evening concerts nightly, capped by the Vermont Jazz Ensemble Street Dance on Saturday.
📍 Middlebury Village Green, Middlebury, VT
🕐 Annual, third week of July | All events free
Now in its late 20s as an annual tradition — 70+ craft vendors and artisans on the Bristol Town Green, all-day live music at the bandstand, kids' activities, horse-and-wagon rides, food trucks, and the natural excuse to walk through Bristol's downtown shops after. Free admission. Timed perfectly against the fall foliage. Presented by the Addison County Chamber with the Bristol Recreation Department.
📍 Bristol Town Green, Bristol, VT
🕐 Annual, late September | Free admission
A summer music series on the back lawn of Lincoln Peak Vineyard in New Haven — local musicians, food trucks, Vermont wine, and enough room to spread a blanket and stay a while. The "Locals Night" version runs the last Friday of every month year-round; the summer series is the main event. Tasting room is open Fri–Sun. Free entry to the music. One of the genuinely lovely evenings available in Addison County from June through September.
📍 142 River Road, New Haven, VT
🕐 Fridays through summer | Tasting room Fri–Sun 12–6pm | Free music
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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One of the best farmers markets in Vermont, running every Saturday on the Mad River Green since 1993. Over 50 vendors — local farms, prepared food, baked goods, artisan crafts, Vermont beer, cider, and spirits. Regulars include Von Trapp Farmstead, Sage Farm Goat Dairy, Mad River Distillers, Mad River Donuts, South Mountain Crepes, and Sunshine Valley Berry Farm. Live local music every week. Rain or shine. Dogs on leash welcome. SNAP/EBT, Farm to Family, and Crop Cash accepted.
📍 Mad River Green, VT Route 100, Waitsfield, VT
🕐 Saturdays 9am–1pm | Mid-May through mid-October | Rain or shine | Free