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Music in Addison County

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Brandon Inn — Free Music Nights

Brandon

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

Red Clover Ale Co. — Thursday Open Mic

Brandon

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

Sister Wicked

Brandon

A clothing and gem shop that doubles as one of the best live music venues in the area. Saturday night concerts (full bands, electric), acoustic jam circles right in the store. No cover.

📍 3 W. Seminary Street, Brandon, VT 🕐 Mon–Sat | Concerts from 8pm Saturdays

Festival on the Green

Middlebury

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
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Bristol Harvest Festival

Bristol

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
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Lincoln Peak Vineyard — Friday Night Music

New Haven

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
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