Craft Shows & Fairs in Woodstock, Vermont

Woodstock sits at the heart of the Upper Valley, a corridor of historic villages in Windsor County where craft shows and artisan events have deep roots. The Woodstock Apples and Crafts Fair is approaching its 50th edition — a milestone that reflects the staying power of this community event. Six miles east in Quechee (Hartford), the Hot Air Balloon, Craft & Music Festival has been running since 1979 as New England's longest-running balloon festival. South along the valley, the Chester Festival on the Green and the Weston Craft Show extend the region's craft calendar. For a village of roughly 3,000 people, Woodstock anchors a remarkably active stretch of Vermont's craft show map.

Woodstock's Craft Events

The Woodstock Apples and Crafts Fair is the signature event. Reaching its 50th edition milestone, it draws 100+ vendors featuring Vermont crafts, specialty food, and food trucks. Admission is $5. The fair is held in October (2025 dates: October 11-12), timed to fall foliage season when tourism traffic through the village peaks. The mix of handmade goods and local food reflects Woodstock's identity as a place where agricultural tradition and artisan culture meet.

The Quechee Hot Air Balloon, Craft & Music Festival at Quechee Green Park in Hartford — just six miles from Woodstock village — runs Father's Day Weekend in June (2026 dates: June 19-21). Established in 1979, it features 50+ craft artisans and vendors alongside hot air balloon launches, live music, and family programming. It is one of the few Vermont events where craft shopping happens under a canopy of rising balloons.

Vermont Crafts Council member studios in Windsor County participate in Open Studio Weekend twice a year (Memorial Day Weekend and first weekend of October), giving visitors a chance to meet makers in their working spaces across the Upper Valley.

The Upper Valley Craft Corridor

Woodstock's craft appeal extends to the surrounding villages. Chester, about 30 miles south, hosts the Chester Festival on the Green — now in its 37th+ year, with 70+ artisans selling 100% handmade work, free admission. Weston, 30 miles southwest, is home to the Weston Craft Show at the Weston Playhouse on Route 100, now in its 28th year (2026 dates: October 7-9). These shows share an audience with Woodstock visitors, and many craft travelers plan multi-stop trips through the corridor during fall foliage season.

The Upper Valley also bridges Vermont and New Hampshire — Hanover, NH (Dartmouth College) is just 18 miles east. This cross-state connection means Woodstock craft events draw from both sides of the Connecticut River.

Best Times to Visit Woodstock for Craft Events

Nearby Cities for Craft Shows

• Burlington — ~90 miles northwest; Church Street Marketplace; Good Trade Makers Market (December); Champlain Valley Craft Show (October)
• Stowe — ~65 miles north; Stowe Foliage Arts Festival (October, 150+ juried artisans)
• Manchester — ~55 miles southwest; Manchester Fall Art and Craft Festival (Hildene Meadows, 200+ juried artisans)
• Bennington — ~75 miles southwest; Bennington Mayfest (May, 120+ vendors)
• Brattleboro — ~55 miles south; Putney Craft Tour (Thanksgiving weekend); Cotton Mill artisan studios

Frequently Asked Questions

When is the Woodstock Apples and Crafts Fair?

The Woodstock Apples and Crafts Fair is held in October, timed to fall foliage season. The 2025 dates were October 11-12. The fair features 100+ vendors with Vermont crafts, specialty food, and food trucks. Admission is $5.

What is the Quechee Balloon Festival?

The Quechee Hot Air Balloon, Craft & Music Festival is New England's longest-running hot air balloon festival, established in 1979. It runs Father's Day Weekend in June at Quechee Green Park in Hartford, VT — six miles east of Woodstock. The festival includes 50+ craft artisans and vendors alongside balloon launches, live music, and family activities. 2026 dates are June 19-21.

Are there other craft shows near Woodstock?

The Chester Festival on the Green (~30 miles south, 70+ artisans, 100% handmade, free admission) and the Weston Craft Show (~30 miles southwest, Weston Playhouse, 28th year) are natural companion events during fall. The Stowe Foliage Arts Festival (65 miles north) and Manchester Fall Art and Craft Festival (55 miles southwest) are within day-trip range. Vermont Crafts Council Open Studio Weekend activates studios across Windsor County twice a year.

Is Woodstock a good base for craft show travel in Vermont?

Woodstock's central Upper Valley location makes it a strong base for reaching multiple events. Chester, Weston, Quechee, and Hanover NH are all within 30 miles. Manchester and Brattleboro are under an hour's drive. During fall foliage season, several major craft shows run within the same week or two, making multi-stop trips practical.

Find Events in Woodstock

CraftShow Events covers craft shows, artisan fairs, and event listings in Woodstock, the Upper Valley, and across Vermont. Search by date and event type to find the Apples and Crafts Fair, Quechee Balloon Festival, and events throughout the region.