Day trip from Jersey · Woodstock
Things to Do in Woodstock, NY: Tinker Street, Overlook Mountain and an Old Arts Colony
Things to do in Woodstock, NY: Tinker Street, WAAM, Bearsville Theater, the Overlook Mountain trail and Opus 40, plus why the 1969 festival was in Bethel.
By Tessa Moretti, our virtual host
Researched and edited by the Chefbouyon team
Updated · 8 min read
Quick picks
- For art loversWoodstock Artists Association & Museum (WAAM)A membership art museum on Tinker Street, founded in 1919.Directions
- For a live showBearsville TheaterA theater on 16 acres in Bearsville with a full calendar of concerts.Directions
- For a mountain hikeOverlook Mountain TrailA 2.4-mile climb past hotel ruins to a summit fire tower at 3,140 feet.Directions
- For something unusualOpus 40A sculptor's lifework of dry-stone walls in an old bluestone quarry, open weekends April through November.Directions
- For book loversThe Golden NotebookA Tinker Street bookstore with a local-authors section and a book club.Directions
Woodstock, New York, has been an artists' town for more than a century, long before the famous festival borrowed its name. A short main street, Tinker Street, curves past galleries, boutiques and cafés. A small triangular village green sits at the center. Behind it all, Overlook Mountain rises over the hamlet, wooded and close enough to climb before lunch.
If you're planning things to do in Woodstock, NY, here's the honest headline first. The 1969 Woodstock festival didn't happen here. It took place on a former dairy farm in Bethel, in Sullivan County, now home to Bethel Woods Center for the Arts. Woodstock the town is something quieter and older: an arts colony founded in 1902, a hand-built concert hall from 1916, and an artists' museum that has been showing local work since 1919.
From North Jersey, Woodstock is a straight run up the New York State Thruway toward Kingston. From Manhattan, Trailways buses leave from Port Authority. It's a long day trip, so many people make it a weekend. If you're coming up the Hudson anyway, my guides to Beacon and Cold Spring are good stops on the way.
How I picked these
These picks come from research, not first-hand visits. I used each venue's own website, the Town of Woodstock, New York's Department of Environmental Conservation and reputable sources, and confirmed each place was active in 2025–2026. The list leans on Woodstock's arts history, with one hike and two short drives.
Tinker Street and the arts colony
Most of Woodstock's shops sit along a few blocks of Tinker Street, Mill Hill Road and Rock City Road, meeting at the Village Green. Travel writers describe a mix of brightly painted boutiques, artisan shops, restaurants and plenty of festival-era tie-dye. Park once and walk.
The Village Green is the small triangle where those three streets meet, and it's the town's natural meeting point. Depending on the day, visitors describe musicians playing there or an outdoor market setting up, and it's where the Trailways bus stops, so car-free visitors start their day right in the middle of things. Use it as your compass. WAAM, The Golden Notebook and the Guild office are all a short stroll along Tinker Street, and the Woodstock Playhouse sits a little south on Mill Hill Road. Plan a loose loop: galleries first, then lunch, then the shops, saving the drive up Meads Mountain Road or out to Bearsville for later in the day.
Woodstock Artists Association & Museum (WAAM)
Known for A membership art museum founded in 1919 that shows Woodstock artists past and present.
28 Tinker St, Woodstock, NY 12498
Checked against official sources Nov 2026
The Woodstock Artists Association & Museum, known as WAAM, is at 28 Tinker Street, right in the middle of town. It was founded in 1919 as a not-for-profit membership organization for the visual arts, and it still exhibits artists working in and around Woodstock alongside its historic collection.
The late-2026 lineup shows its range. "Feathered Friends: A Woodstock Aviary" runs from October 23, 2026, to January 3, 2027. Several other shows, including "Figuring It Out" and "Z Behl: The Mule's Vision," run through November 29. WAAM lists hours of noon to 5 p.m., Thursday through Sunday, and it closes on major holidays.
Who'll love it: anyone who wants to understand why artists moved here in the first place. Nearby: The Golden Notebook across the street, and the Village Green a short stroll away.
The Golden Notebook
Known for A Tinker Street bookstore with staff picks, a book club and sections for local authors and Hudson Valley interest.
29 Tinker St, Woodstock, NY 12498
Checked against official sources Nov 2026
The Golden Notebook is the bookstore at 29 Tinker Street. Its site highlights staff picks, a Golden Notebook Book Club, a shelf of local authors and a Woodstock and Hudson Valley interest section, which makes it a good place to find a book about the town you're walking through. It also posts upcoming events through its newsletter.
Who'll love it: readers and gift shoppers. Nearby: WAAM and the rest of Tinker Street. For a bookstore crawl closer to home, see my guide to New Jersey bookstores.
Woodstock Byrdcliffe Guild
Known for The nonprofit arts center carrying on the Byrdcliffe Arts Colony, founded in 1902 on Arts and Crafts ideals.
34 Tinker St, Woodstock, NY 12498
Checked against official sources Nov 2026
Woodstock's arts story begins with Byrdcliffe. The Byrdcliffe Arts Colony was founded in 1902 on Arts and Crafts ideals, and the Woodstock Byrdcliffe Guild carries on that legacy as a nonprofit arts center. Its office is at 34 Tinker Street. The Guild runs exhibitions, an artists-in-residence program, ceramics and jewelry classes, events and a shop.
The historic colony itself sits up the hill on Upper Byrdcliffe Way. The Guild offers tours of the colony grounds, White Pines (the founders' original home with its preserved ceramics studio), the barn and studios. Tours are by appointment, for groups of six or more, and the Guild asks you to call at least a month ahead. Artists' residences aren't open to visitors.
Who'll love it: history and craft lovers, and anyone curious about how a utopian art colony shaped a town.
Music and theater
Woodstock's reputation as a music town is well earned, and you can still hear it live most weekends.
Bearsville Theater
Known for A theater and event space on 16 acres in Bearsville with a busy live-music calendar.
291 Tinker St, Woodstock, NY 12498
Checked against official sources Nov 2026
Bearsville Theater sits on 16 acres a few miles west of the center, at 291 Tinker Street in the hamlet of Bearsville. It describes itself as "an exceptional and unique theater and event space" less than two hours from New York City, and its calendar is full. Late 2026 shows include Hiss Golden Messenger, Ani DiFranco, Loudon Wainwright III, Rickie Lee Jones, and two nights of Gillian Welch and David Rawlings on December 15 and 16.
Who'll love it: music fans who'd rather see a show in a woodsy room than an arena. Book ahead, as some nights sell out.
Woodstock Playhouse
Known for A nonprofit theater established in 1938, with a summer theatre festival, concerts and holiday shows.
103 Mill Hill Rd, Woodstock, NY 12498
Checked against official sources Nov 2026
The Woodstock Playhouse was established in 1938 by Robert Elwyn and still stands at the entrance to town, at 103 Mill Hill Road. It's a nonprofit that calls itself an "iconic site of American theatre and music history." Its summer theatre festival runs from early June to mid-August, and it hosts concerts, gallery shows and productions by the New York Conservatory for the Arts.
Coming up, the Woodstock Symphony Orchestra performs Schubert and Rimsky-Korsakov's Scheherazade on Saturday, November 7, and the Conservatory stages A Christmas Carol – The Musical on December 11, 12 and 13. Check the Playhouse site for tickets.
Who'll love it: families, theater fans and anyone planning a cozy December weekend.
Maverick Concerts
Known for The oldest ongoing summer chamber music festival in the U.S., in a hand-built 1916 wooden hall.
120 Maverick Rd, Woodstock, NY 12498
Checked against official sources Nov 2026
Maverick Concerts is a summer pleasure worth planning a trip around. The writer and philosopher Hervey White founded the festival in 1916, and the barn-like wooden hall was built by hand that year as part of his Maverick Colony. It calls itself the oldest ongoing summer chamber music festival in the U.S., and it also programs jazz, folk, contemporary and world music, plus free Maverick Family Saturdays.
The 2026 season has ended, and the festival says it looks forward to 2027. Watch its site in spring for the summer schedule.
Who'll love it: chamber-music lovers and anyone who likes the idea of a concert in the woods.
Overlook Mountain
Woodstock's mountain is right there above town, and its trail is one of the Catskills' best-loved.
Overlook Mountain Trail
Known for A 2.4-mile climb past the ruins of the Overlook Mountain House to a summit fire tower.
Overlook Mountain Trailhead, Meads Mountain Rd, Woodstock, NY 12498
Checked against official sources Nov 2026
The Overlook Mountain Trailhead is on Meads Mountain Road, with a parking lot on the right about two miles up from the Village Green. New York's Department of Environmental Conservation lists the Overlook Spur Trail as 2.4 miles one way, with a steady, nonstop climb of 1,370 feet.
At 1.6 miles, you reach the ruins of the Overlook Mountain House, a hotel the DEC says was begun in the 1920s and never completed. It is "now being reclaimed by nature," and the DEC asks hikers not to go inside. At the 3,140-foot summit, a historic fire tower waits for the view.
Practical notes from the DEC: stay on the paths, since snakes have been seen; respect the private property near the summit; and follow Leave No Trace. Groups of more than 20 need a permit. Weekend lots fill early in fall, so start in the morning.
Who'll love it: hikers who want a classic Catskills summit without an all-day commitment. For more trails, see my best hikes in New Jersey.
Two short drives
Opus 40 in Saugerties
Opus 40
Known for Harvey Fite's monumental dry-stone sculpture in an old bluestone quarry, set in 63 more acres of meadows and trails.
356 George Sickle Rd, Saugerties, NY 12477
Checked against official sources Nov 2026
Opus 40 is one of the strangest and most beautiful places in the Hudson Valley. In an abandoned bluestone quarry at the foot of Overlook Mountain, sculptor Harvey Fite built a monumental environmental sculpture of dry-stone walls, ramps and terraces using thousands of tons of stone. The sculpture covers more than six acres, and the nonprofit also manages 63 more acres of meadows, quarry trails and historic buildings, including the Fite House and the Quarryman's Museum.
It's at 356 George Sickle Road in Saugerties, a short drive east of Woodstock. Opus 40 is open Saturdays and Sundays, 10 a.m. to 5 p.m., from April through November. The final day of the 2026 season is its Fall Faire on Saturday, November 7, with a rain date of November 8. Fall Faire tickets are limited, so book ahead.
Who'll love it: photographers, families who like to scramble around, and anyone who loves stone and sky.
Bethel Woods: where the festival really happened
Bethel Woods Center for the Arts
Known for The site of the 1969 Woodstock festival, with a museum about the festival and the Sixties and a summer concert pavilion.
200 Hurd Rd, Bethel, NY 12720
Checked against official sources Nov 2026
If you came to Woodstock for the 1969 festival, Bethel Woods Center for the Arts is the place you're actually looking for. The festival took place on a former dairy farm in Bethel, Sullivan County, and drew about 450,000 people over three days, according to the museum. The Museum at Bethel Woods sits on the historic site at 200 Hurd Road, with more than 6,000 square feet of exhibits on the festival and the Sixties, including artifacts, films and a hippie bus.
The museum lists daily hours from April 1 to December 31, with golf-cart tours of the field from May through October and pavilion concerts typically from May through September. It's a cashless venue. Bethel is a long drive from Woodstock, so treat it as a separate day trip rather than an add-on.
Who'll love it: music history fans and anyone who wants to stand on the hillside where it happened.
Getting there
By car from North Jersey: Take the New York State Thruway (I-87) north toward Kingston. The Town of Woodstock says that from Kingston, you follow Route 28 to Route 375, which runs through West Hurley to Route 212 and the Woodstock hamlet. Parking in the center fills quickly on fall weekends.
By bus from NYC or New Jersey: The Town of Woodstock says Adirondack Trailways runs daily buses between Port Authority Bus Terminal and Woodstock, stopping in Kingston, with the stop across from the Village Green. New Jersey riders can reach Port Authority on many NJ Transit bus routes. Locally, Ulster County's UCAT buses are fare-free Monday through Saturday, and Woodstock is on the Z route.
By train: There's no train to Woodstock. The town notes that Amtrak stops at Rhinecliff, across the river from Kingston, and Metro-North's Hudson Line reaches Poughkeepsie. You'd still need a car or taxi from either.
When to go: Fall for foliage, Overlook and big shows; summer for the Playhouse festival and Maverick Concerts; spring and late fall for quieter weekends and Opus 40. Winter is cozy, with WAAM, Bearsville shows and holiday theater.
Stay the night: Woodstock is far enough that an overnight makes sense. Our weekend getaways from NYC guide includes a Woodstock inn, and my weekend getaways in New Jersey guide has ideas closer to home.
Every place in this guide, on the map
- Woodstock Artists Association & Museum (WAAM)28 Tinker St, Woodstock, NY 12498
- The Golden Notebook29 Tinker St, Woodstock, NY 12498
- Woodstock Byrdcliffe Guild34 Tinker St, Woodstock, NY 12498
- Bearsville Theater291 Tinker St, Woodstock, NY 12498
- Woodstock Playhouse103 Mill Hill Rd, Woodstock, NY 12498
- Maverick Concerts120 Maverick Rd, Woodstock, NY 12498
- Overlook Mountain TrailOverlook Mountain Trailhead, Meads Mountain Rd, Woodstock, NY 12498
- Opus 40356 George Sickle Rd, Saugerties, NY 12477
- Bethel Woods Center for the Arts200 Hurd Rd, Bethel, NY 12720
Questions people ask
Was the Woodstock festival actually in Woodstock, NY?
No. The 1969 Woodstock Music and Art Fair took place on a former dairy farm in Bethel, in Sullivan County, a long drive southwest of the town of Woodstock. The site is now Bethel Woods Center for the Arts, whose museum covers the three-day festival, which drew about 450,000 people. The town of Woodstock is a separate place, an arts colony since the early 1900s.
Is Woodstock, NY worth visiting?
Yes, especially if you like small-town art, music and mountains. Woodstock has a walkable center around Tinker Street and the Village Green, a 1919 artists' museum, several active theaters and concert venues, and a classic Catskills hike up Overlook Mountain. Add Opus 40 in nearby Saugerties and you have a full day, or an easy weekend with an overnight.
How long is the Overlook Mountain hike?
New York's Department of Environmental Conservation lists the Overlook Spur Trail as 2.4 miles one way with a steady 1,370-foot climb, so plan on about 4.8 miles round trip. You pass the ruins of the Overlook Mountain House at 1.6 miles and reach a historic fire tower at the 3,140-foot summit. The trailhead lot is on Meads Mountain Road, about two miles above the Village Green.
Can you get to Woodstock, NY without a car?
Yes, by bus. The Town of Woodstock says Adirondack Trailways runs daily service to and from Port Authority in Manhattan, stopping in Kingston, with the Woodstock stop in the hamlet center across from the Village Green. Ulster County's UCAT buses are fare-free Monday through Saturday, and Woodstock is on the Z route. There is no train station in Woodstock.
When is the best time to visit Woodstock, NY?
Fall is the most popular season, with foliage on Overlook Mountain and a busy concert calendar. Summer brings the Woodstock Playhouse theater festival and Maverick Concerts. Opus 40 is open weekends from April through November. Winter is quieter, but WAAM's galleries, Bearsville Theater shows and holiday performances at the Playhouse keep the town lively.
Spot something out of date, or know a place we should add? Tell us. Corrections are read first.
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