Applehead Artist's Cottage Guidebook
Live Music
Just down the hill (within walking distance) is the legendary Bearsville Theater - a historic live music venue and bar that has hosted an array of live national and local acts for decades. It was a part of the original Bearsville Complex owned by Albert Grossman (manager of Bob Dylan) as well as musician Todd Rundgren.
195 locals recommend
Bearsville Theater
291 Tinker StJust down the hill (within walking distance) is the legendary Bearsville Theater - a historic live music venue and bar that has hosted an array of live national and local acts for decades. It was a part of the original Bearsville Complex owned by Albert Grossman (manager of Bob Dylan) as well as musician Todd Rundgren.
The Colony has become a favorite place to see live music, with the newly renovated interior and stage (and sound system). It is a great place to see emerging artists and local acts.
153 locals recommend
Colony
22 Rock City RdThe Colony has become a favorite place to see live music, with the newly renovated interior and stage (and sound system). It is a great place to see emerging artists and local acts.
This place is amazing for many reasons. Not only can you attend outdoor live music events, is a beautifully landscaped, incredibly quiet place to walk and view the amazing sculpture park designed and build by artist Harvey Fite (from April to November) as well as the live music in the summer months. Click on the Events page to view upcoming outdoor concerts
351 locals recommend
Opus 40
356 George Sickle RdThis place is amazing for many reasons. Not only can you attend outdoor live music events, is a beautifully landscaped, incredibly quiet place to walk and view the amazing sculpture park designed and build by artist Harvey Fite (from April to November) as well as the live music in the summer months. Click on the Events page to view upcoming outdoor concerts
This is the gem of Woodstock - an intimate venue for live music with legendary artists. The home of the late Levon Helm (a Woodstock treasure), drummer and singer of The Band. He renovated his barn to host amazing concerts for locals and it turned into a national destination where he would perform almost nightly with the likes of Donald Fagan, Elvis Costello, Larry Campbell, Amy Helm, and more.
98 locals recommend
Levon Helm Studios
160 Plochmann LnThis is the gem of Woodstock - an intimate venue for live music with legendary artists. The home of the late Levon Helm (a Woodstock treasure), drummer and singer of The Band. He renovated his barn to host amazing concerts for locals and it turned into a national destination where he would perform almost nightly with the likes of Donald Fagan, Elvis Costello, Larry Campbell, Amy Helm, and more.
A beautiful setting for open air concerts in the summer (classical, jazz and children's music). This is the oldest running chamber music festival site in the US (over 100 years ago it opened it's doors) and is one of Woodstock's first two arts colonies (and an attempt at a utopian society). Watch their videos on the "history" page on their website - they are inspiring.
63 locals recommend
Maverick Concerts Inc
120 Maverick RdA beautiful setting for open air concerts in the summer (classical, jazz and children's music). This is the oldest running chamber music festival site in the US (over 100 years ago it opened it's doors) and is one of Woodstock's first two arts colonies (and an attempt at a utopian society). Watch their videos on the "history" page on their website - they are inspiring.
Spiegeltent Bard
60 Manor AveOn the other side of the Hudson but worth the drive
Food scene
On the fancier side of things - Silvia is a wonderful restaurant for a birthday or a romantic dinner. Great bar too. Located in the center of town - you can walk to local shops and bars and farmers market nearby
275 locals recommend
SILVIA
42 Mill Hill RdOn the fancier side of things - Silvia is a wonderful restaurant for a birthday or a romantic dinner. Great bar too. Located in the center of town - you can walk to local shops and bars and farmers market nearby
Another great restaurant with a great menu and bar - a couple of miles from town center
226 locals recommend
Red Onion
1654 NY-212Another great restaurant with a great menu and bar - a couple of miles from town center
Quaint and amazing vegan restaurant in the village green. You don't have to be a vegan to love this place! Outdoor patio. Bar too.
234 locals recommend
Garden Cafe Woodstock
6 Old Forge RdQuaint and amazing vegan restaurant in the village green. You don't have to be a vegan to love this place! Outdoor patio. Bar too.
A beautiful restaurant with views of the creek. It was once the legendary Bear Cafe (owned by Albert Grossman) now a Mexican restaurant. Haven't eaten here yet but I have enjoyed the atmosphere.
168 locals recommend
The Bear Cafe
295A Tinker StA beautiful restaurant with views of the creek. It was once the legendary Bear Cafe (owned by Albert Grossman) now a Mexican restaurant. Haven't eaten here yet but I have enjoyed the atmosphere.
Literally at the bottom of our hill - walking distance. If you like BBQ this is a good spot. Great bar. Outdoor seating is great for socially distanced dining.
69 locals recommend
Dixon Roadside
261 Tinker StLiterally at the bottom of our hill - walking distance. If you like BBQ this is a good spot. Great bar. Outdoor seating is great for socially distanced dining.
Hiking trails and public swimming holes
Climb to the top to see the ruins of the Overlook Mountain House (old hotel that has burned down three times since it's erection) and make it to the top and climb the fire tower for amazing Catskill views!
222 locals recommend
Overlook Mountain
Climb to the top to see the ruins of the Overlook Mountain House (old hotel that has burned down three times since it's erection) and make it to the top and climb the fire tower for amazing Catskill views!
Ashokan Reservoir
Great for easy walking / biking. Scenic.
Great for easy walking / biking. Scenic.
141 locals recommend
Ashokan Rail Trail- Woodstock Dike Trailhead
1285 NY-28Great for easy walking / biking. Scenic.
Beautiful and easy hike - in the center of town along the Sawkill creek
31 locals recommend
Comeau Trail
Comeau TrailBeautiful and easy hike - in the center of town along the Sawkill creek
Millstream Swimming Hole
Big Deep
Laundry drop off
Woodstock Laundry
59 Mill Hill RdDrop off service here - pretty quick turnaround!
Local essentials
Woodstock Meats
57 Mill Hill RdLocal butcher with some groceries - center of town
CVS
60 Mill Hill RdPharmacy hours 9am- 8pm
Hannaford Supermarket
295 NY-375Sunfrost Farm
217 Tinker StVery nearby - great produce! Great juice bar and cafe too.
Great natural foods grocery - a little on the spendy side but good produce and health food!
202 locals recommend
Sunflower Natural Foods Market
75 Mill Hill RdGreat natural foods grocery - a little on the spendy side but good produce and health food!
We like this place better than CVS - a more personal and small town experience!
13 locals recommend
Village Apothecary
79 Tinker StWe like this place better than CVS - a more personal and small town experience!
Drinks
I love this place for drinks! The indoor and outdoor vibe is amazing.
97 locals recommend
Early Terrible
45 Mill Hill RdI love this place for drinks! The indoor and outdoor vibe is amazing.
Good Night
15 Rock City RoadHealth and Wellness
Glo Spa Woodstock
62 Ricks RdVery nearby and great spot.
A favorite yoga studio. Check for outdoor classes for social distancing too.
14 locals recommend
Woodstock Shakti Yoga
1685 Sawkill RdA favorite yoga studio. Check for outdoor classes for social distancing too.