Drinks & Nightlife
Bearsville Theater
291 Tinker StGreat gigs, good food, and a unique setting.
Well if there is something going on at "The Barn" it's probably gonna be good. A really wonderful venue and worth a visit. In case you're not familiar with local musical history, Levon was a founding member of The Band. His daughter, Amy Helm, is a frequent performer. If the Midnight Ramblers are doing a gig, don't miss it.
98 locals recommend
Levon Helm Studios
160 Plochmann LnWell if there is something going on at "The Barn" it's probably gonna be good. A really wonderful venue and worth a visit. In case you're not familiar with local musical history, Levon was a founding member of The Band. His daughter, Amy Helm, is a frequent performer. If the Midnight Ramblers are doing a gig, don't miss it.
Colony
22 Rock City RdSome great gigs, most nights. Go early if you want a seat.
Keegan Ales
20 St James StGood brew!
Woodstock Brewing
5581 NY-28Good local brewery!
Food Scene
An upscale American diner! Excellent food, down home atmosphere.
Good, Italian food plus designer type pizzas all very good. The veranda is lovely in summer
297 locals recommend
Cucina
109 Mill Hill RdGood, Italian food plus designer type pizzas all very good. The veranda is lovely in summer
Great lunch and breakfast. Pick up a loaf of bread or some sweets.
203 locals recommend
Bread Alone Bakery
22 Mill Hill RdGreat lunch and breakfast. Pick up a loaf of bread or some sweets.
Funky, fun, informal. They have a guest chefs- never quite know what's cooking, but always good, fun, relaxed. Call and ask what's cookin.
159 locals recommend
The Pines
5327 NY-212Funky, fun, informal. They have a guest chefs- never quite know what's cooking, but always good, fun, relaxed. Call and ask what's cookin.
Yum Yum Noodle Bar - Woodstock
4 Rock City RdGood Asian food, friendly service.
Great food, lovely drive up to Big Indian. They use local as much as possible.
440 locals recommend
Peekamoose
8373 NY-28Great food, lovely drive up to Big Indian. They use local as much as possible.
Ok, maybe the 2nd best pancakes on the planet. #1 is still Pamela's in Pittsburgh, Pa. Dylan 's breakfast spot when he lived up this way, so they say.
108 locals recommend
Sweet Sue's
49 Main StOk, maybe the 2nd best pancakes on the planet. #1 is still Pamela's in Pittsburgh, Pa. Dylan 's breakfast spot when he lived up this way, so they say.
SILVIA
42 Mill Hill RdVery good food, lovely veranda. One of our best
Creekside dining in the ever expanding Bearsville Theatre Complex. Fun place, good food. Nancy's Ice cream (GOOD!) is just the other side of the building.
167 locals recommend
The Bear Cafe
295A Tinker StCreekside dining in the ever expanding Bearsville Theatre Complex. Fun place, good food. Nancy's Ice cream (GOOD!) is just the other side of the building.
Good pizza! If you want to bring food back to the cabin, this place is close and fast. Take away pasta is a HUGE serving and pretty good- enough for 2 unless you're really hungry. A bit pricey.
8 locals recommend
Woodstock Pizza Theater
138 Tinker StGood pizza! If you want to bring food back to the cabin, this place is close and fast. Take away pasta is a HUGE serving and pretty good- enough for 2 unless you're really hungry. A bit pricey.
Good Night
Excellent Asian, tending toward Vietnamese or Thai- but kinda unique. Beautiful terrace.
Medo
Very good Japanese
Theatre, food, drink. From $ to $$$$. Lotsa fun. Creek side dining. Some great gigs. All in a venue originally planned by Al Grossman.
195 locals recommend
Bearsville Theater
291 Tinker StTheatre, food, drink. From $ to $$$$. Lotsa fun. Creek side dining. Some great gigs. All in a venue originally planned by Al Grossman.
Excellent bread, best coffee in the area, nice sandwiches and pastries. Order your bread online for pick up! They sell out!
62 locals recommend
Kingston Bread + Bar
43 N Front StExcellent bread, best coffee in the area, nice sandwiches and pastries. Order your bread online for pick up! They sell out!
Parks & Nature
For x-country, this place is wonderful! They rent equipment also.
Fabulous Views. Parking can be difficult on busy days. Well worth a few hours. Snow spikes advised for winter hiking. Available online or at Haust hardware in town.
Overlook Mountain Trail
Overlook Mountain TrailFabulous Views. Parking can be difficult on busy days. Well worth a few hours. Snow spikes advised for winter hiking. Available online or at Haust hardware in town.
Onteora Lake
Great place for a swim. No developed beach, but a real gem.
Big Deep
Well hardly a beach, but a great swimming hole
Kaaterskill Falls Trail Head
New York 23AGood hike.
Great trail along the reservoir. No hills! Perfect for walking, running, biking, x-country skiing.
140 locals recommend
Ashokan Rail Trail- Woodstock Dike Trailhead
1285 NY-28Great trail along the reservoir. No hills! Perfect for walking, running, biking, x-country skiing.
Mountain Trails Cross Country
6198 Main StEntertainment & Activities
Funky, wonderful, and good films. Go early, have dinner in town and then catch a film. Parking can be tricky, so go early.
94 locals recommend
Upstate Films Woodstock
132 Tinker StFunky, wonderful, and good films. Go early, have dinner in town and then catch a film. Parking can be tricky, so go early.
Great festival in June. For 2017- Tom Petty and Steve Miller Band, plus many others. Book early- rooms are at a premium. Hunter is a very pretty 40 minute drive from Guardian Guest House
mountain Jam
7740 Main StGreat festival in June. For 2017- Tom Petty and Steve Miller Band, plus many others. Book early- rooms are at a premium. Hunter is a very pretty 40 minute drive from Guardian Guest House
Woodstock Playhouse
103 Mill Hill RdLive plays, musicals, and music gigs.
Town Tinker Tube Rental
10 Bridge StFun, pretty fast in the spring.
Wonderful music in an amazing setting. Summer only. World class string quartets. Jazz. Folk. Great spot!
63 locals recommend
Maverick Concerts Inc
120 Maverick RdWonderful music in an amazing setting. Summer only. World class string quartets. Jazz. Folk. Great spot!
Arts & Culture
A fantastic festival in October. Book early. Every room in Woodstock is filled for the festival weekend.
22 locals recommend
Woodstock Film Festival Inc
13 Rock City RdA fantastic festival in October. Book early. Every room in Woodstock is filled for the festival weekend.
Traditional design Tibetan Buddhist Monastery. Great bookstore if you are into Tibetan Buddhist art and books. Just up the road from us, across from the parking lot for Overlook Trail. Visitors always welcome.
71 locals recommend
Karma Triyana Dharmachakra Tibetan Buddhist Monastery
335 Meads Mountain RdTraditional design Tibetan Buddhist Monastery. Great bookstore if you are into Tibetan Buddhist art and books. Just up the road from us, across from the parking lot for Overlook Trail. Visitors always welcome.
Essentials
Great selection of local and homegrown foods, specialty items, great soup. Also stocks milk, eggs, butter, etc. About 5 minutes away, and has pretty much everything you need.
160 locals recommend
Sunfrost Farm
217 Tinker StGreat selection of local and homegrown foods, specialty items, great soup. Also stocks milk, eggs, butter, etc. About 5 minutes away, and has pretty much everything you need.
All organic, all natural. A really well stocked natural food market.
201 locals recommend
Sunflower Natural Foods Market
75 Mill Hill RdAll organic, all natural. A really well stocked natural food market.
Hannaford Supermarket
295 NY-375Closest supermarket