Erika & Nehemiah
Things To Do
Ashokan Rail Trail
New York City's water supply system can be traced back to the Ashokan Reservoir, a short drive from Woodstock. The Ashokan Rail Trail, an 11.5-mile multi-use trail used year-round for walking, biking, cross-country skiing, and snowshoeing, is also peppered with signage that sheds light on the history and culture of the Catskill Mountains and the creation of the reservoir. Open daily, sunrise to sunset year-round.
Overlook Mountain Hike
Overlook Mountain is one of the more popular hiking spots in the area. Climb to the top to find the ruins of an old Catskills hotel, a sky-piercing fire tower, and a truly awe-inspiring view of the Hudson Valley. Overlook Mountain features a higher difficulty 3-hour, 5-mile round trip hike, with an elevation gain of about 1,370 feet (Peak elevation: 3,140 feet). *Difficulty level: Difficult, but the Best Views in Woodstock.*
Swimming Holes
More of a summer activity, but the area’s watering holes are one of its biggest draws. The Millstream is right downtown and one of the most popular. Big Deep is not far and a bit larger. Fawn’s Leap is further afield but very gorgeous.
Wilson Campground
Completely surrounded by the beautiful Catskill mountains, with panoramic views creating a picturesque setting, Kenneth L. Wilson Campground offers secluded, wooded campsites and many outdoor activities. Campers can enjoy a hike on the nature trails or ride on the mountain bike trail (for advanced riders), and nearby villages offer numerous shops and restaurants, as well as inner-tubing the river.
Opus 40 Sculpture Park
A retired art professor from Bard and quarryman named Harvey Fite spent 37 years building this six-acre maze of a sculpture out of bluestone. Fite worked alone, using only hand tools. The site is now a sculpture park and museum, and an awesome place to spend a morning or afternoon.
Stroll along Tinker Street
Tinker Street is the main artery that runs right through the center of Woodstock's charming main town. On either side, visitors will find galleries; shopping; restaurants; and architectural remnants of Woodstock's centuries-old past, like the Woodstock Reformed Church, which is from the mid-19th century. A stroll down Tinker Street will give visitors the quintessential Woodstock sightseeing experience all in one street.
Station Bar and Curio
Located in an old train station in Woodstock, NY, Station Bar & Curio is the perfect spot to relax with a cold craft beer or cocktail after a day out in the Catskills. Sip a glass of wine on their covered outdoor patio, sample spirits from regional distilleries while shooting pool, and enjoy a light meal made from locally sourced ingredients as you admire their rotating collection of antiques, junk, and local art.
Oriole 9
Casual cafe that serves eclectic breakfast & lunch fare featuring produce from the owners' organic farm.
Bread Alone Bakery
Famous local bakery with great breakfast sandwiches, bagels, sweat treats, soups, and bread
Cucina
Cucina is a modern Italian restaurant located in a farmhouse with adorable front porch seating. The cocktails are delicious, and the pizza and pasta are fantastic. This spot does get busy, so be sure to put in a reservation.
Silvia
SILVIA is a family-owned restaurant that connects food & people with back-to-basics cooking that is honest, sustainable, and refined. Their open kitchen, with a wood-fired grill and pantry of organic vegetables, reflects our dedication to locally-sourced ingredients.
Good Night
From the family that brought you Silvia, a new sister is born. An ode to all who appreciate and celebrate the love of the family meal, embracing the act of sharing. Good Night offers an array of globally inspired fresh vibrant dishes that are based around South East Asian cuisine with a modern twist. The room is designed for comfort with a nod to romance and most importantly, joy. Whether an intimate meal for two or a gathering of 20 or more, you can be sure that yours will be a Good Night.
Dixon Roadside
Dixon Roadside prides itself in offering the highest quality products from local Hudson Valley and Catskills' farms and small businesses. Our menu is comprised of comfort food classics with an occasional modern and fresh twist.
Tinker Street Tavern
The Peterson House was originally built in 1897 and reimagined in 2021 as Tinker Street Tavern. The house sits on an iconic property at the beginning of Tinker Street in the historic hamlet of Bearsville within the town of Woodstock. It is surrounded by native bluestone and the soothing sounds of the Sawkill Creek. The property is an oasis unto itself where locals and visitors alike can gather for good conversation and great music along with cold beer and delicious cocktails.