Woodstock: a plain guide to the town
Updated September 22, 2026
Woodstock is spread out: farms, stone walls and a long stretch of Route 169, one of the prettiest drives in the state. There's no downtown to speak of, so this guide is organised around the places people actually drive to — the historic house across from the common, the fairgrounds, the winery and the farms.
Roseland Cottage
The pink Gothic Revival house across from the town common, built in 1846 as a summer home for Henry C. Bowen and now a National Historic Landmark owned by Historic New England. The grounds include a parterre garden, an icehouse, a garden house, a carriage barn and the oldest surviving indoor bowling alley in the country. All visits to the house are by guided tour; the grounds are open to walk and picnic on.
- Address: 556 Route 169, Woodstock. 860-928-4074.
- Season and tours (2026 listing): Thursday–Sunday, June 4–October 25, tours on the hour 11 a.m.–3 p.m. Closed July 4 and October 16, 22 and 23.
- Admission: $20 adults, $17 seniors, $7 students and children, free for Historic New England members.
- Parking is behind the barn; follow the signs.
The Woodstock Fair
Connecticut's largest agricultural fair and one of its oldest, held every Labor Day weekend at the fairgrounds in South Woodstock. It opens at 4 p.m. on the Thursday before Labor Day and runs through Monday: livestock and agricultural shows, two stages, a midway and a family area.
- Fairgrounds: 281 Route 169, South Woodstock. 860-928-3246.
- Gate times: Thursday from 4 p.m., Friday from noon, Saturday–Monday from 9 a.m.
- There is no fair parking on site. Neighbouring lots — Fairvue Farm, Valleyside Farm, South Woodstock Baptist Church, Scranton's Shops — charge $10 and set their own prices.
Taylor Brooke Winery and Brewery
A farm winery and brewery on Route 171 with a tasting room and a heated four-season pavilion, open year-round. Full details, hours and visiting rules are in our wineries guide.
- 818 Route 171, Woodstock. 860-974-1263.
- Winery: Friday 2–6:30 p.m., Saturday noon–6 p.m., Sunday noon–5:30 p.m., closed Monday–Thursday.
What we're still confirming
Roseland Cottage's tour season is set fresh each year, and the fair's hours can change; both are taken from their own pages for the current season. We haven't published Woodstock town office or library hours here because we'd rather print nothing than print a stale schedule — check the town's site. If something here is wrong, tell us and we'll fix it the same week.