Town
Where to Stay in Woodstock
The 1969 festival was held in Bethel, about 60 miles away, but the town kept the name's fame. It had been an artists' colony since 1902, when Ralph Radcliffe Whitehead founded Byrdcliffe, and generations of painters, musicians and writers have lived here since. Tinker Street has galleries, boutiques, restaurants and crystal shops, busy on summer weekends, with a working arts scene behind them. The Overlook Mountain trail starts just outside the village, a 5-mile round trip to a fire tower and the ruins of the Overlook Mountain House hotel. The Woodstock Way Hotel is built around a 15-foot waterfall on Tannery Brook, a short walk from Tinker Street. Twin Gables, on Tinker Street, has been an inn since 1926, The Woodstock Inn on the Millstream has 19 rooms and 3 cottages, and Hotel Dylan, a renovated 1960s motel, is about 10 minutes' drive from the village.
The Woodstock Inn on the Millstream
Woodstock, NY · Inn
Nineteen rooms and suites plus 3 cottages on Tannery Brook Road, a short walk from Woodstock's village center. The property began as a 1940s motel and sits beside the Millstream, with gardens and hammocks along the water. Every room has a private entrance, and a continental breakfast focused on local food is included. The cottages (Brookside Bungalow, Corner Cottage and Hillcrest House) can be booked for stays of up to a month.
The Woodstock Way Hotel
Woodstock, NY · Boutique Hotel
A small hotel on Tannery Brook in Woodstock, built around a 15-foot waterfall and a short walk from Tinker Street and the village center. Rooms have turntables with artist-curated vinyl, Bose speakers, floor-to-ceiling windows and private outdoor space. There is no restaurant on site; the village's restaurants are a few minutes on foot. No pets. The sister property, Kingston Carriage House, is 25 minutes south. Listed in the MICHELIN Guide.
Twin Gables of Woodstock
Woodstock, NY · Guesthouse
A 10-room guesthouse at 73 Tinker Street in the center of Woodstock, in an 1880s Victorian house that Alfred Daiber and his wife opened as an inn in 1926. It reopened in 2019 and is now part of the {verdigreen} group, with sister properties including Hotel Mountain Brook and Phoenicia Lodge. Interiors have hand-painted murals, vintage furniture and a parlor with a fireplace, and there is a rooftop terrace used for yoga. A breakfast of local baked goods and fruit is included.
Hotel Dylan
Woodstock, NY · Boutique Motel
A 1960s roadside motel about 10 minutes' drive from Woodstock village, renovated by Woodstock native Paul Covello with rooms designed by Robert and Courtney Novogratz. Its 22 rooms are named for musicians connected to Woodstock and have Crosley turntables, with records and board games to borrow from the front desk. There is a heated saltwater pool from Memorial Day to Labor Day, fire pits on the lawn, and an on-site Mexican restaurant and bar, Santa Fe Woodstock.
Why Stay in Woodstock
- •Byrdcliffe and the Woodstock Artists Association & Museum have run programs since the early 1900s, and they still do.
- •Tinker Street has many galleries and independent shops within a few blocks.
- •The Overlook Mountain trail starts just outside the village, a 5-mile round trip to a fire tower with views over the Hudson Valley.
- •A useful base for the Phoenicia–Kingston corridor, without committing to a more remote address.
What Makes This Area Interesting
- •Overlook Mountain Trail: 5 miles round trip from Meads Mountain Road; a fire tower at the top and the hotel ruins near the summit.
- •Phoenicia: 20 minutes west on Route 28; Foxfire Mountain House and the Esopus Creek for a day away.
- •Kingston: about 20 minutes southeast; the Stockade District and the Rondout waterfront.
- •Levon Helm Studios: Saturday night Rambles when in session; book well in advance.
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