48 Hour Getaway in Upstate NY | Weekend Retreat in Woodstock NY

Posted by Dylan Taft on Tuesday, March 28th, 2017 at 10:34am.

Are you looking for a weekend escape from New York City? Some place that you can get outside, get some fresh air and just escape for a few days? Whether you’re a music lover or self proclaimed hippie or not, Woodstock, NY is a great place to visit, no matter your passions, and in any season.



Day 1:

Let the journey begin! It’s only a short two hour drive from New York City to Woodstock, so you can still make it to your destination for dinner if leaving straight from the office on a Friday night! After the picturesque drive upstate through the Hudson Valley, make your way to Hotel Dylan to settle in and get some shut eye for an exciting weekend ahead. Hotel Dylan (www.thehoteldylan.com) is nestled off of Route 28 in Woodstock, in an area that some people refer to as the ‘Gateway to the Catskills’.  The rooms here are brightly and uniquely decorated, with each room named after a rock n’ roll legend, and a laid back, bohemian, very Woodstock-y feel about them. An outdoor courtyard with movie screenings, hammocks, fire pits, and seasonal pool create a fun, communal environment to hang out in warmer months. After settling in to your night 1 digs, grab dinner at Santa Fe Woodstock, a popular Mexican restaurant and bar located on the grounds of Hotel Dylan, where together, it’s all about “peace, love, and tacos.” Santa Fe Woodstock is the extension of the very popular Santa Fe restaurants located in Tivoli and in Uptown Kingston and are known for their modern Mexican cuisine, legendary guac and killer margaritas.


Day 2:

After a continental breakfast at Hotel Dylan, it is time to get out and explore Woodstock on a one-on-one level (and hopefully the margaritas the night before don’t delay that too much!) Hotel Dylan sits at the base of the Catskills and is 10 minutes from one of the most popular local hiking trails, Overlook Mountain, in the Indian Head Mountain range (with trailhead parking on Meads Mountain Road). The complete trail loop contains over 9 miles of trail but is truly popular for its places of interests along the way, such as the Overlook Mountain Hotel Ruins (the remains of a grand hotel that could have rivaled the likes of the Mohonk Mountain House in nearby New Paltz), the Overlook Mountain Fire Tower (climb to the top for unparalleled views of the Hudson Valley, Catskills and Ashokan Reservoir), and Echo Lake. If the weather doesn’t happen to cooperate with your visit and snow is expected, the Overlook Mountain trails are also popular snowshoeing and cross country skiing trails as well (or if snow looks to considerably change your plans, Woodstock is a great homebase for skiers and snowboarders and there’s plenty of Hudson Valley slopes nearby to consider as well!)


After your morning hike, the exploration continues- this time into the village to get a glimpse at what life is like really like in Woodstock. Re-fuel at one of the many village eateries offering breakfast or lunch, like Joshua’s Cafe, a well loved Mediterranean cafe and restaurant with plenty of sandwich, salads and Middle Eastern and Mediterranean specialities where you can try something new, or find a new spin on a traditional favorite. The village of Woodstock is a great place to stroll around after a more intense morning hike- there’s plenty of unique, tie-dyed shops to explore, like Candlestock or Woodstock General Supply, and if you hang out near the village green long enough, you may even meet who the New York Times calls “Grandpa Woodstock,” spreading peace and love around the village.     

Because it is located within walking distance, now would be a good time to check into your next home for the night; the Woodstock Inn on the Millstream (www.woodstock-inn-ny.com). This quaint and peaceful Inn is located on the idyllic SawKill, a lush, gardened haven only minutes away from the heart of the village where you can recharge your batteries. With 18 rooms, standalone cabins and bungalows, albeit small, The Woodstock Inn on the Millstream is the most popular bed and breakfast in the town.

You couldn’t well come to Woodstock without squeezing in some kind of music or entertainment related activity, now could you? Just 2 miles down the road from your new digs on Tinker Street is the Bearsville Theatre, where you may be able to catch a show highlighting some of the local musical talent of our area (their event schedule is located on their website at www.bearsvilletheatre.com). The Little Bear, on the Bearsville theatre grounds, has great Chinese fare, with an enclosed patio overlooking the stream for a romantic dinner setting. Also, even closer to the Inn, only ½ a mile away is the Woodstock Playhouse, a venue featuring a range of plays, productions, festivals and other musical acts (their schedule of events can be found at www.woodstockplayhouse.org). If after a long day of exploration, your only wish is to be wined and dined, take a drive to New World Home Cooking for more culinary exploration, where chef Ric Orlando (who has been featured on and has won multiple Food Network competition challenges) features a new and extensive specials menu every night, with tons of gluten-free and vegan options as well.

Day 3:

Time to check out of your cozy inn by the stream and pack up as your weekend away draws to a close. With a short commute back to real life though, you’ve still got time to catch some more sights on your way back home!

After a lazy morning brunch in the village at Oriole 9, where they serve unique takes on breakfast all day long, it’s time to start making your way out of town. Only 10 minutes out of Woodstock, in nearby West Saugerties (conveniently as you start making your way back to the New York State Thruway) is Opus 40, a unique sculpture park and museum, open seasonally, where one man, (a Bard College Fine Arts founder, Harvey Fite) turned an abandoned quarry into a stunning Blue Stone labyrinth built completely by hand using ancient Mayan techniques. Opus 40 depicts the beauty of Woodstock’s natural surroundings, this time enhanced by man to near perfection. Walk the grounds and the museum showing Fite’s tools and techniques, and then it’s back to the road to get back to the city by dinnertime.




Woodstock is a great weekend retreat destination, but for those who love it as much as we do, occasional weekend visits may just not be enough! If you’ve ever considered making Woodstock a more permanent part of your life, give Taft Street Realty a call; we’re happy to help you find the Woodstock vacation home, investment property or full time-residence that you’ve always dreamed about!

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