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  • Writer's pictureChelsea Susan Bednar

Top 10 Reasons to visit Twin Gables of Woodstock

Updated: Mar 2, 2022

Pack up your guitar, catch the midnight train, and escape to a place that will turn back in time to 1969! It’s a little town you may have heard of, Woodstock, NY (yes, THAT Woodstock), home of the infamous music festival and of Twin Gables Guest House.

Established as a residence for artists in 1926, Twin Gables set its roots in the artistic community. Under new ownership since 2019, TG has been lovingly restored and redesigned to honor those artistic roots. Centrally located in the historic downtown, most tourist destinations are all a short commute - from local hiking trails to eclectic boutiques and delicious eateries, there’s enough for everyone to find their own rhythm.

1: Groove to the Beat:

When it comes to festivals there’s the one that started it all: from hosting world famous musicians to up and coming talent, modern day Woodstock has upheld its legacy when it comes to music and entertainment.

With roots as a venue to host artists and musicians, the historical Colony (.3 mi Woodstock, NY) continues to host many live performances throughout the year. With the giant beer garden, outdoor stage, open mike nights, a billiards room, and a full kitchen/bar, you’ll happily find yourself there until closing. New on the music scene is Pearl Moon (.3 mi Woodstock, NY), a restaurant that hosts live music events and dance nights. Classic, tried and true is Levon Helm's The Barn which brings travelers from far and wide to our little hamlet.

For musicians wanting to explore the instrumental side of the town, the Woodstock Music Shop (.2 mi Woodstock, NY) is for you! Vinyl collectors and instrument lovers will definitely find something to bring home.

You can’t visit Woodstock without making an homage to where it all started, the site of the original festival at Bethel Woods Art Center (19 mi Bethel, NY) . On their page you can download a digital map that shows the grounds from 1969 and today. For your photo-op moment, you can stop at the roadside attraction, the Woodstock Festival Monument Plaque that commemorates the history of the location.

2: Stay stylin, babe:

What’s better than small town boutiques? The local shopping scene has an impressive selection of retail therapy to choose from, all within short walking distance from TG! For an iconic “hippie” souvenir, be sure to stop by our neighbor, Headstock & Co.! Thrifters will love Castaways(.3 mi),, a local consignment & resale shop where you’ll be sure to find a hidden gem. Three Turtle Doves, Rock City Vintage(.2 mi), and Narnia Vintage (.3 mi) are a must for vintage lovers. For an artsy gift, Timbuktu(.2 mi), Lovewild Designs(.3 mi), and Lily’s Boutique (1 min walk) are good places to start.

3: Get spiritual, man!

As this is Woodstock, there are many magical/metaphysical shops to explore. Stock up on handmade tinctures and natural herbs at Modern Mythology(.2 mi), have a spiritual reading at Everyday Magic(.1 mi), or crystal shop and read up on all things witchy at Mirabai (.2 mi) of Woodstock. Of course you can't miss the iconic Candlestock(.2 mi), known for handmade beeswax candles and their popular giant drip candle mountain - you can buy a candle and add to the sculpture yourself!

4: Reconnect with Mother Nature:

Welcome mother nature and venture through some of the many local hiking trails in the area. Behind the property and up the road is the Comeau Trail(200 ft); this easy trail parallels the water, providing a calming background noise to your reconnection with nature. If you're searching a unique experience, walk the ART Trail (Ashokan Rail Trail)(4.5 mi West Hurley, NY), an old railroad that winds through the woods and to a breathtaking overlook of the Ashokan Reservoir. If you set aside a good part of the day, you can hike up the Overlook Mountain Trailhead(2.8 mi Woodstock, NY). Once you reach the top, you can climb the Historic Fire Tower for unbelievable view of the Hudson River and tour the incredible ruins of the Overlook Mountain House.

5: In the Spotlight:

Spend a lovely evening at the theatre! The Woodstock Playhouse (.6 mi ) greets you as you drive into the town - you can’t miss it! The venue hosts concerts for the Rock Academy and the Woodstock Symphony throughout the winter months, and is home to the Woodstock Playhouse Summer Theatre. See their website for their current performance calendar and to reserve tickets for upcoming events.

6: Seasonal Events:

Kicking off the summer is the The Woodstock Film Festival. This foundation celebrates with an annual festival along with year round programming providing educational opportunities and artistic outreach to both emerging & established filmmakers. Catch a deal on crafts, antiques, and collectables at Mower's Flea Market(.2 mi ). This event starts in the spring and runs every Saterday/Sunday through the end of the summer. Dance to the rhythm every Friday or Sunday evening from 4-6pm at the Woodstock Drum Circle at the Village Green(.2 mi)- join in the festivities! In the summer months partake in seasonal activities such as the Woodstock Farm Festival or attending a show at the Woodstock Drive-In outdoor screenings. In Autumn, be sure to witness the Woodstock Halloween Parade that walks through the main street.

8: The Food Lover’s Choice:

A little known secret is how incredible of a foodie town Woodstock is!! From the casual eateries to the more upscale restaurants, there is something that will satisfy everyone’s tastebuds all within a short walking distance from our property.

If you’re jonesing for a coffee and a bagel in the morning, try The Mud Club (.3 mi) or Moonrise Bagels(.1 mi). For something grab & go, try a house-made smoothie from Little Apple Café or a bowl of savory meatballs from Sharkie’s(.2 mi) (who have an insanely delicious chik-pea “meatballs” for the vegetarians out there). For brunch, The Garden Café(.2 mi) and Oriole 9 (.2 mi) are the perfect choices.

Wine and dine for an evening! Cucina(.7 mi) is a Italian restaurant featuring a contemporary menu, set in a renovated farmhouse. They have both indoor and outdoor seating, with outside heaters for when the weathers colder. Silvia(.3 mi) is a family run restaurant that sources organic ingredients, features an in house wood-fired grill, and provides plenty of indoor & patio covered outdoor seating. Their sister property is Good Night(.2 mi), a Southeast Asian inspired restaurant that provides an ambient, retro atmosphere to sip on a cocktail and dine in for the evening.

9: Local Brews & Bars:

Indulge in some apps & taps at Woodstock Brewing (12 mi Phoenicia, NY); relax and enjoy selections from a full food menu and up to 15 in-house brews.

Looking for a night cap? The Station Bar & Curio (.1 mi) is where it's at late night - a local's favorite, the eclectic decor, games, billiards room, and live music events will keep you curious and entertained throughout the evening. Early Terrible (.3 mi) is the sister property to the previously mentioned Mud Club; this rustic, whimsically designed establishment will wow you with their speciality cocktails and delectable appetizers. Sit by one of their many fire pits and enjoy your food on their large outdoor courtyard.

10: Rest & Rejuvenate at Twin Gables Guest House:

Ah, your day of movin' and grooving' has come to an end, so rest and relax at Twin Gables of Woodstock. Our warm and welcoming innkeeper LeAnn will be sure to make you feel right at home. Keep the fun going by putting on a record, pouring yourself a glass of wine, and playing board games for a nice night in. Rather, prepare some tea from the coffee nook and cozy up next to the fireplace in The Parlor with a good book from our curated collection. Featured in The Gables is the Meditation Room - follow the rainbow stairs on the second floor to this little oasis where you can meditate, practice yoga, or treat yourself to a specialty massage (by appointment only). In the morning, enjoy a selection of baked goods from a local bakery along with fresh fruit, juice, yogurt, and other assorted breakfast items. Before you head out, become a part of our history and sign our guest book! We love the stories you have to tell - keep in touch by tagging us on social media and using the hashtag #littlearthotel. Until we see you next... peace, love, and rock and roll!

Looking to come back to town? Try staying at one of our sister properties upstate in Tannersville and East Chatham with {verdigreen} Hotels .

Remember to follow TG on Instagram and Facebook, and tell us about your stay over at Trip Advisor. Come visit us at Twin Gables of Woodstock and enjoy the groovy vibes!

Thank you for reading,


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