Applehead Artist's Cottage Guidebook

Jason
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.
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Bearsville Theater
291 Tinker St
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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.
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.
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Colony
22 Rock City Rd
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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.
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
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Opus 40
356 George Sickle Rd
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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
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.
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Levon Helm Studios
160 Plochmann Ln
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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.
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.
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Maverick Concerts Inc
120 Maverick Rd
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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.
On the other side of the Hudson but worth the drive
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Spiegeltent Bard
60 Manor Ave
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On 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
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SILVIA
42 Mill Hill Rd
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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
Another great restaurant with a great menu and bar - a couple of miles from town center
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Red Onion
1654 NY-212
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Another 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.
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Garden Cafe Woodstock
6 Old Forge Rd
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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.
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.
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The Bear Cafe
295A Tinker St
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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.
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.
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Dixon Roadside
261 Tinker St
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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.

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!
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Overlook Mountain
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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!
Great for easy walking / biking. Scenic.
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Ashokan Reservoir
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Great for easy walking / biking. Scenic.
Great for easy walking / biking. Scenic.
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Ashokan Rail Trail- Woodstock Dike Trailhead
1285 NY-28
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Great for easy walking / biking. Scenic.
Beautiful and easy hike - in the center of town along the Sawkill creek
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Comeau Trail
Comeau Trail
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Beautiful and easy hike - in the center of town along the Sawkill creek
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Millstream Swimming Hole
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Big Deep
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Laundry drop off

Drop off service here - pretty quick turnaround!
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Woodstock Laundry
59 Mill Hill Rd
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Drop off service here - pretty quick turnaround!

Local essentials

Local butcher with some groceries - center of town
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Woodstock Meats
57 Mill Hill Rd
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Local butcher with some groceries - center of town
Pharmacy hours 9am- 8pm
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CVS
60 Mill Hill Rd
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Pharmacy hours 9am- 8pm
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Hannaford Supermarket
295 NY-375
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Very nearby - great produce! Great juice bar and cafe too.
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Sunfrost Farm
217 Tinker St
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Very 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!
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Sunflower Natural Foods Market
75 Mill Hill Rd
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Great 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!
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Village Apothecary
79 Tinker St
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We 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.
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Early Terrible
45 Mill Hill Rd
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I love this place for drinks! The indoor and outdoor vibe is amazing.
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Good Night
15 Rock City Road
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Health and Wellness

Very nearby and great spot.
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Glo Spa Woodstock
62 Ricks Rd
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Very nearby and great spot.
A favorite yoga studio. Check for outdoor classes for social distancing too.
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Woodstock Shakti Yoga
1685 Sawkill Rd
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A favorite yoga studio. Check for outdoor classes for social distancing too.