Our Mini-Moon Guide to Woodstock, New York

By Over The Moon

Written by Jackie Martin

We hear you. You are not ready to hop on a plane just yet, but your thirst for celebrating your love with a romantic getaway is insatiable. A mini-moon makes perfect sense for right now. Luckily, there is a chic, safe and accessible option for north-easterners—Woodstock, New York. By car from NYC, you can get to this storied Catskills town in just two hours, yet feel like you’re 1,000 miles away. Historically, the destination has been known for its incomparable music history and outdoor activities. Yet now, the destination is flourishing with the development of higher-end establishments. According to Darryl Jack, the general manager of Hotel Dylan, “The significant growth of fine dining opportunities in the last 10 years has been staggering.” Plus, there’s been a healthy influx of chic boutique hotels, wineries, and breweries making it even more enticing to visit.

Below, our tried and true (and safe) guide to Woodstock, New York:


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Where to Stay

When traveling to Woodstock—a town synonymous with music—it’s only natural to stay at a hotel that celebrates just that. Just five minutes from the charming main street of Woodstock, Hotel Dylan is a property designed to spark the senses through colorful design and rich music history. Designed by celebrated husband and wife design duo, The Novogratz, the property was transformed from an abandoned motel into a vibrant retreat, where each room is named after one of the rock n’ roll greats associated with Woodstock 1969. Whether it’s The Van, The Bowie, The Janis, etc., you’ll be sure to feel the music and art of the time period. Or, couples can opt for The Artist’s Suite, a haven boasting a garden shower, double sinks, fireplace, and vaulted ceilings. It’s important to emphasize how impeccably clean the rooms are and how naturally designed for social distancing the entire property is.

Though the hotel’s free spirit vibe remains true, there is no gray area in their stringent measures to carry out the best practices for their guests. The hotel has utilized the latest room sanitization technology, enforces masks being worn in public spaces, and has expanded the downtime for rooms. “A large part of our reputation is the cleanliness of the property,” notes Jack. Outdoors, they’ve also added fire pits, where you can take in the fresh Catskills air while enjoying a glass of vino and making s’mores with the curated sets the property provides to all guests.


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If you’re looking to stay in the heart of town, The Herwood Inn is a creative and hip spot just steps away from shops and restaurants. Book the colorful two-room King Suite, which boasts a private patio and a claw foot soaker tub.


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Situated behind the Tannery Brook Waterfall, Woodstock Way Hotel is another magical property just steps away from the storied town. Also inspired by art and music, you’ll instantly feel the energy of the destination’s rich history through the design and amenities in each room. And for a peaceful feel, wake up to the sound of the cascading waterfall rushing through your chic, yet rustic room.

Where to Eat

Pick up a fresh baguette, chocolate croissant or Green Egg Sandwich at Bread Alone, a family-owned, values-driven bakery steps from the village green. (OTM Tip: Before you leave, be sure to stop back here and bring a bit of the Upstate home with you by buying one of their famous fresh Certified Organic sliced breads.)


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For a laid-back lunch or dinner option, right off Tinker Street (a.k.a. the main shopping street), you’ll find Early Terrible, a restored barn with an outdoor courtyard. At this gem of a place, cozy up near the fire pits while enjoying their Stormy Mojito and one of the delicious dishes like the Wood Fired Burger or Shrimp Kebab.

The Garden Cafe is a cozy vegan spot in the heart of town where you can enjoy outdoor dining in a beautiful garden. From smoothies to paninis all made with organic ingredients, this is also a great place to pick up a fresh juice to enjoy while scoping out the stores in town.


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For a sophisticated dinner, book a reservation at SILVIA, a family-owned restaurant dedicated to carefully sourced ingredients from local farms. Sit outdoors and take in the energy of the town while enjoying dishes from their wood fired grill and organic vegetable-centric pantry.

Satisfy your sweet tooth with a treat from Peace Love & Cupcakes, a charming little shop off Tinker Street. The best part? The cupcakes are named after classic rockers like Janis Joplin, Arlo Guthrie, and Jimi Hendrix. Another spot not to miss for its superb quality is Nancy’s of Woodstock Artisanal Creamery and Coffee House. Enjoy coffee or handcrafted ice-cream with very spacious seating outdoors.


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What to Do

During your music-inspired stay, visit Bearsville Center—home to the spirit of Woodstock—founded by legendary music entrepreneur Albert Grossman. Grossman managed some of the most popular and successful performers of the 1960s and created Bearsville to be a place where musicians could live, work, eat and play. The Bear Cafe and surrounding enterprises, set in 15 acres, were visited by many key players in the world of folk-rock and rock & roll including the likes of Bob Dylan, Janis Joplin, The Band, and Gordon Lightfoot.

After checking out the vintage stores and art galleries, a trip to world-famous, outdoor sculpture park and museum Opus 40 is a requisite stop during your romantic getaway. There, you can explore six-and-a-half acres of earthwork sculpture, 50 acres of meadows, forested paths and bluestone quarries while taking in brilliant views of the Catskill Mountains. To boot, Opus 40 is a prime location for social-distancing.

Overlook Mountain Trail is an incredible 4.6-mile round trip hike with several staggeringly beautiful lookout points. While being fully immersed in nature, you’ll also eventually come across mountain house ruins for a property that was never finished and a historic fire tower. The Overlook Mountain Wild Forest offers a unique combination: a historic fire tower, mountain house ruins, and impressive views of the Hudson River Valley and the central Catskills all within an under five-mile hike.

For another type of activity, head 30 minutes by car to Accord, New York, to visit Westwind Orchard & Cidery. Revered as a bio-intensive farm and organic oasis, this one-of-a-kind spot is dedicated to making distinctive ciders that are unfiltered and made without any added sulfites. There, you’ll also find exquisite Italian pasta and pizza dishes to pair with your drink, making for the ideal date night. That’s amoré!