Checked October 8, 2026. Hours shift with the season, so call before you drive.
Woodstock sits at the foot of Overlook Mountain on the southeast edge of the Catskills, in Ulster County. It has been an artists’ town since 1902, when the Byrdcliffe colony went up on the slope above the village, and it’s still more galleries, bookshops and porches than anything else. Tinker Street and Mill Hill Road meet at the village green, and nearly everything you’ll walk to is within a few blocks of it.
One thing to settle first: the 1969 festival didn’t happen here. It happened in Bethel, about an hour and a half southwest. More on that below. For the mountain towns to the north, see our Hunter, Tannersville, Phoenicia and Windham field guides.
Woodstock at a glance
- Go for: the Overlook fire tower, Tinker Street on a weekday morning, and a long dinner on Mill Hill Road.
- Stay: two nights. One for the mountain, one for the galleries.
- Car: yes. The village is walkable, but Overlook, Opus 40 and everything else aren’t.
- This weekend: the last weekend of the season for open fire tower cabs, and the WAAM Members Studio Tour.
- Next week: the Woodstock Film Festival, October 14 to 18. Book dinner early.
- From Clove Creek: about 35 minutes.
Things to do in Woodstock, NY this fall
1. Overlook Mountain
Trail · Overlook Spur Trail to the fire tower
- Distance: 2.4 miles each way, on an old carriage road.
- Climb: about 1,370 feet, gradual but steady the whole way. There’s no flat stretch to rest on, so first-timers find it harder than it sounds. Pace yourself.
- Top: the 1950 fire tower at 3,140 feet, with a side path to a ledge over the Hudson Valley and the Ashokan Reservoir. For a flat walk along that water, the Ashokan Rail Trail starts about 10 minutes from the green.
- Park: the small lot on Meads Mountain Road, or DEC’s Meads Meadow lot half a mile on. About 10 minutes from the green.
- Fee: none, per DEC.
- From Clove Creek: about 45 minutes.
Overlook is one of the three busiest spots in the whole Catskill Forest Preserve, and the parking shows it. The trailhead lot fills early on fall weekends, and long stretches of Meads Mountain Road and part of Macdaniel Road are posted no-parking, with a $150 fine and towing in some zones. If the main lot is full, drive half a mile on to DEC’s Meads Meadow lot, which has about 30 spaces and a half-mile connector trail. Better still, go on a weekday, or be at the trailhead by 8.
At 1.6 miles you pass the shell of the Overlook Mountain House, a hotel begun in the 1920s and never finished. Look from outside, as DEC asks. The tower’s stairs are open all year. The cab at the top opens only when Catskill Fire Tower Project volunteers are there, on weekends and holiday Mondays through this Indigenous Peoples Day weekend, October 10 to 12. After that, it’s the stairs and the platform. Check the DEC Overlook Mountain Wild Forest page before you go.
Watch for rattlesnakes. The mountain is timber rattlesnake habitat, and the species is threatened in New York. Stay on the road, be careful around rock ledges and the ruins, and keep dogs leashed. They’re slow and not looking for trouble. Give them room.
What we bring for Overlook
Map
Catskill Park Trails Illustrated Map
National Geographic #755, waterproof. Shows Overlook, Echo Lake and the trails beyond, with no signal needed.
Knees
Cascade Mountain Tech Carbon Trekking Poles
The carriage road is steady going up and long going down. Poles save your knees on the way back.
Light
LHKNL Rechargeable Headlamp, 2-pack
Sunset comes early in October, and the woods get dark before the road does. USB-C charging.
2. Tinker Street and the arts
Start at the green and walk west on Tinker Street. The Woodstock Artists Association and Museum (28 Tinker St) has been showing local artists for more than a century and is open Thursday to Sunday, noon to 5. This weekend, October 10 and 11, is its Members Studio Tour, when artists open their own studios around town. Above the village, Byrdcliffe, the arts and crafts colony founded in 1902, is still run by the Woodstock Byrdcliffe Guild, and you can walk its roads on your own.
3. Karma Triyana Dharmachakra
The Tibetan Buddhist monastery across from the Overlook trailhead welcomes visitors. Its shrine room is worth a quiet look on your way up or down the mountain. Shoes come off at the door, and some rooms close during teachings, so check the KTD calendar.
4. Opus 40
Opus 40 is a dry-stone sculpture covering more than six acres of an old bluestone quarry, the life’s work of one sculptor, Harvey Fite. It’s about 11 minutes away in Saugerties, open Thursday to Monday, 10 to 5 (last entry at 4), through November. Wear shoes with grip, because the bluestone gets slick when it’s wet.
5. The Woodstock Film Festival, next week
The 27th Woodstock Film Festival runs October 14 to 18, with screenings in Woodstock, Saugerties, Kingston and Rosendale. Rooms and dinner tables get scarce that week, so book early if you’re coming for it, or avoid it if you’re coming for quiet.
The 1969 festival was in Bethel, not Woodstock
The Woodstock Music and Art Fair was held in August 1969 on Max Yasgur’s dairy farm in Bethel, Sullivan County. The organizers first hoped to hold it near Woodstock, which is where the name came from, but it ended up about 67 miles southwest. There’s no festival field in town.
If you want to see where it happened, the Museum at Bethel Woods sits on the festival grounds and is open daily from 10 to 5 through December 31. It’s about an hour and a half from Woodstock by car, so it’s a day trip, not an afternoon add-on.
Woodstock restaurants and coffee
Most of it is on Tinker Street and Mill Hill Road (Route 212), a short walk from the green. Some kitchens close one or two weekdays, so plan food around midweek hours.
- Oriole 9 (17 Tinker St). The breakfast-and-lunch place in the middle of the village. Dine in or take it to the green.
- Shelter (21 Mill Hill Rd). Wood-fired Argentine cooking. Closed Wednesday, dinner only on Thursday from 5, and brunch from noon to 4 on weekends. Live music on Friday nights.
- SILVIA (42 Mill Hill Rd). The reservation dinner in town. Book ahead, especially during the film festival.
- The Garden Cafe (6 Old Forge Rd). Organic vegan food and a juice bar, just off the green.
Parking in the village: the town lot on Rock City Road charges on busy weekends. There are free town lots off Tannery Brook Road and Comeau Drive, a short walk from Tinker Street.
Where to stay near Woodstock, NY
Our cabin · Hunter, NY · 35 minutes
Clove Creek Cabin
About 35 minutes from the village green by Route 214, Route 28 and Route 212, past Phoenicia. It sits between two creeks, with a hot tub, a sauna and an indoor fireplace, two queen bedrooms, an Ooni pizza oven and a Solo Stove fire pit on about 600 square feet of deck. Dogs are welcome when they’re on the reservation. Cell service is close to none, but the Wi-Fi is strong and handles Wi-Fi calling.
It suits two couples who want Overlook and Tinker Street by day and a quiet creek and a sauna at night.
Clove Creek is run by Unplugged Cabins, our sister brand.
Nearby · Tannersville · about 40 minutes
Blue Heron
A quiet two-bedroom cabin a five-minute walk from Tannersville’s Main Street. Sleeps four, takes dogs, and has a fire pit and a real workspace. It’s about 40 minutes to Woodstock over Platte Clove Road, which closes for winter in mid-November. The long way around takes closer to 50.
It suits a couple splitting a weekend between Woodstock’s galleries and the high peaks around Tannersville.
Coming soon · Jefferson, NY · about 1 hr 30 min to Woodstock
Juniper Ridge
We’re building a modern tiny cabin on Blenheim Hill, near Jefferson in Schoharie County, on about five private acres of maple, beech and birch forest. It’s a single-story, 361-square-foot studio with a full bath, a kitchenette and a small covered porch. The plan includes a hot tub under the trees, a wood-fired sauna, a fire pit and a private trail through the woods.
- Getting there: about 1 hour 30 minutes from Woodstock, by Route 212, Route 28 and Route 42, then Route 23A, Route 23 and Route 30. That’s a long way for a Woodstock weekend, so think of it as a base for the northern and western Catskills instead.
- Close by: Mine Kill State Park and Stamford, each about 15 minutes away.
- Where it stands: footings went in in September, and the cabin is being built in the workshop now. The opening date isn’t set yet.
It suits two people who want the quieter western Catskills, with Woodstock as one long day out.
It isn’t open yet. Join the list and you’ll hear first when it opens.
Juniper Ridge is run by Unplugged Cabins, our sister brand.
Rather stay in town? Woodstock Way Hotel has rooms looking onto a waterfall, close to the village center. The Woodstock Inn on the Millstream on Tannery Brook Road has 19 rooms and a few cottages, with breakfast. Hotel Dylan, on the south edge of town, has 23 rooms and a seasonal pool. More ideas in our Catskill cabin rentals guide.
Pack for cold nights
Woodstock is lower and milder than the mountain towns to the north, but October nights still drop fast once the sun goes behind Overlook. Our packing list lives on the Gear page: camping essentials for cold nights, from a warm bed to a camp kitchen that actually works.
One perfect day
Coffee in the car and at the Overlook trailhead by 8, before the lot fills. At the fire tower by 10, with the Hudson Valley spread out below. Down by noon, a quiet stop at the monastery across the road, then lunch at Oriole 9 and an afternoon on Tinker Street and at WAAM (Thursday to Sunday). Dinner on Mill Hill Road, then the drive north to a hot tub.
Woodstock FAQ
Was the 1969 Woodstock festival in Woodstock, NY?
No. The Woodstock Music and Art Fair took place in August 1969 on Max Yasgur’s dairy farm in Bethel, in Sullivan County, about 67 miles southwest of the town of Woodstock, or roughly an hour and a half by car. It was first meant for the Woodstock area, which is where the name came from. The festival site is now Bethel Woods Center for the Arts, with a museum that is open daily from 10 to 5 through December 31.
How long is the Overlook Mountain hike?
The Overlook Spur Trail is 2.4 miles each way on an old carriage road, climbing about 1,370 feet at a steady grade, per DEC. You pass the ruins of the Overlook Mountain House at 1.6 miles and reach the 3,140-foot fire tower at the top. Most people take three to four hours round trip.
Where do you park for Overlook Mountain?
The main trailhead lot is on Meads Mountain Road, across from the Karma Triyana Dharmachakra monastery, about 2.5 miles up from the village green. It is small and fills early on fall weekends. The overflow is DEC’s Meads Meadow lot, half a mile farther on Macdaniel Road, with about 30 spaces and a half-mile connector trail. Don’t park on the road: long stretches of Meads Mountain Road and part of Macdaniel Road are posted no-parking, with a $150 fine and towing in some zones.
Are there rattlesnakes on Overlook Mountain?
Yes. DEC’s management plan for the Overlook Mountain Wild Forest lists the timber rattlesnake, a threatened species in New York, as present, and its trail page warns that snakes have been seen. Stay on the carriage road, watch where you put your hands around rock ledges and the hotel ruins, and keep dogs leashed and close. If you see one, give it room and leave it alone. They are protected.
How far is Woodstock from New York City?
About 100 miles, or a little over two hours by car without traffic. Take the Thruway north to exit 19 at Kingston, then Route 28 west, Route 375 north and Route 212 into the village. Exit 20 at Saugerties and Route 212 west works too.
Where should you stay near Woodstock?
In town there’s the Woodstock Way Hotel, the Woodstock Inn on the Millstream, and Hotel Dylan on the south edge of town. Our cabin, Clove Creek in Hunter, NY, is about 35 minutes away, with a hot tub and a sauna. Blue Heron in Tannersville is about 40 minutes over Platte Clove Road while it’s open for the season.