People live in New York City to grow their careers, experience world-class restaurants and entertainment, and participate in a diverse melting pot of cultures. But the stone jungle can wear on you, and it’s refreshing to trade in the skyscrapers for some maple trees every now and then.

That’s where Ulster County, New York comes in. Spanning the Catskill Mountains and the Hudson River Valley, Ulster offers many small towns to visit, mountains to hike, and homey places to eat and drink. Two hours from NYC, this area has green space in spades and is easily reachable from the city by car. Read on for recommendations on booking your next getaway to this natural reprieve from the city.

Explore Ulster County’s Local Towns

Ulster County has several small enclaves that feature local shopping and sights as you breathe in the crisp rural air. Check out these three local towns to get a feel for the area’s charm.

New Paltz, NY

 “Local” and “sustainable” are more than buzzwords here. New Paltz is known for its farm-to-table cuisine and historic preservation of natural resources. Its Main Street is lined with shops, boutiques, and cafes and is home to the college town of SUNY New Paltz. Huguenot Street is not to be missed, with 10 acres (four hectares) of beautifully preserved 17th-century dwellings, buildings, and artifacts. If you travel in the fall, be sure to check out some candlelight ghost tours.

New Paltz has a vibrant and well-known outdoor scene, which we’ll get into below when talking about the Mohonk Preserve. But one part worth seeing is the Testimonial Gateway—a massive stone archway and watchtower that served as the formal entrance to the Mohonk Mountain House from 1908 to 1935. The Mountain House, also described further on, is a literal Victorian castle built atop the Shawangunk Mountain Ridge.

It’s also worth checking out the Rosendale Trestle, which is a 12-minute drive outside the city in Rosendale. The Trestle is a 940-foot (286-meter) continuous truss bridge that rises 150 feet (45 meters) above Rondout Creek. Once used for the Wallkill Valley Railroad, it’s now a pedestrian walkway with great views of the surrounding area.

Kingston, NY

Ulster County’s capital is a historic town with much to explore. New York state’s first capital, Kingston dates to the mid-1600s and was burned by the British during the American Revolution. The city has three historic districts with buildings dating to the colonial era. In fact, The Four Corners at the intersection of John and Crown Streets feature four stone houses built before the war, between 1663-1775.

Kingston is perfect for walking around and admiring all its old buildings. There are plenty of shops and restaurants, including small boutiques for local wares (more on the food later). One of my favorite things to do is visit Rough Draft Bar & Books. This rustic tavern-shop offers draft beer and cider, coffee, wine, baked goods, and books for all ages to read and purchase. The city is also littered with plenty of wall murals worth touring as you walk around.

Woodstock, NY

While you may know it for the famous outdoor music festival, you’d be surprised to know that the 1969 Woodstock Music and Art Fair didn’t take place here, but rather in Bethel, about 1.5 hours away. Still, Woodstock is something of a bohemian destination. It certainly has its own music and arts scene, as you’d expect. For starters, Levon Helms Studio is a must-see for music lovers—listen to live music acts inside of its large, renovated barn. Bob Dylan fans will want to visit the studios’ Big Pink room, where Bob Dylan and The Band recorded The Basement Tapes, and The Band wrote their album Music from Big Pink.

The town also has plenty of local shops on Tinker Street (the main drag of downtown), with plenty of boutiques to scour. For visual arts, try Opus 40, an outdoor landscape sculpture park about a 10-minute drive from the town. Created over 37 years by pioneering artist and professor Harvey Fite, Opus 40 is a world-famous nonprofit sculpture park and museum with more than 60 acres (24 hectares) of meadows, forested paths, and bluestone quarries—including 6.5 acres (2.6 hectares) of earthwork sculpture.

Discover the Rustic and Stylish at Ulster County Accommodations

When deciding where to spend the night in Ulster, try one of these accommodations (or all of them!) that lean in to the culture and style of the Middle Hudson River Valley.

Hasbrouck House (Stone Ridge, NY)

Hasbrouck House is an 18th-century Dutch Colonial stone mansion that offers a modern luxury escape from the city. It features 25 bedrooms across four buildings and several places to dine, including an in-house locally-sourced restaurant called Butterfield, The Cauldron Bar outdoor lounge, and an outdoor burger and salad shack during the warmer months. Some of the best features include a 100-year-old pool and over 50 acres (20 hectares) of land for you to explore, with a private lake area.

Mohonk Mountain House (New Paltz, NY)

It’s hard to mention accommodations in the Hudson Valley without Mohonk Mountain House, a literal Victorian castle all-inclusive resort in Ulster County. What’s particularly stunning about this hotel is its location atop the crest of the Shawangunk Ridge, surrounded by thousands of acres of forests and nestled on Lake Mohonk. Amenities include rooms with fireplaces and stunning views, a golf course, a spa, an indoor and outdoor pool, as well as ice rinks and trails.

Bed and Breakfasts (Various)

If you’re looking for less of a luxury visit, there are plenty of affordable Bed and Breakfasts in the area. Some of our favorites are The Arbor Bed and Breakfast and A Serene Vista Spa Bed and Breakfast. The Arbor is in High Falls, NY, and has rooms in a renovated old farmhouse. It’s hosted by Nancy Greenwald, a horticulturist and garden designer. A Serene Vista is a relaxing “mindfulness and spa” BNB, surrounded by a 700-acre (283-hectare) horse farm with a nice view atop Shawangunk Ridge.

Hike Mountains and Lake Trails in Ulster County

One of the most popular things to do in Ulster County is to hike the beautiful and expansive natural landscape. With more than 750,000 acres (300,000 hectares) of protected lands, this area of New York offers more than 350 miles (563 kilometers) of trails within Catskill Park alone.

Minnewaska State Park Preserve

Starting on the dramatic Shawangunk Mountain Ridge 2,000 feet (600 meters) above sea level, drive to the Minnewaska Preserve for plenty of carriage roads and 50 miles (80 kilometers) of footpaths. This area offers several sky lakes (be sure to check out Lake Minnewaska) and waterfalls, as well as rock climbing, horseback riding, and cross-country skiing in the winter. One of the most popular areas is Sam’s Point, located on the highest section of the Shawangunks and featuring a dramatic overlook over pristine pine forests. Paid parking is available in several areas of the park.

Mohonk Preserve

Close to Minnewaska is the Mohonk Preserve in New Paltz, which is larger and contains the world-famous Gunks cliffs. This area is home to the previously mentioned Mohonk Mountain House, and resort guests get a free pass to the 85 miles (136 kilometers) of footpaths. Visitors who aren’t staying at the Mountain House will need to purchase a day pass to access the trails, with different price points for hikers and those who want to bike, climb, or horseback ride.

Ashokan Reservoir

Going further north, the Ashokan Reservoir offers several more accessible hikes with a view. The reservoir is one of several created to source water to New York City, and this one provides 40% of the total supply. The Ashokan River Trail is open year-round and offers 11.5 miles (18.5 kilometers) of path along the reservoir. If you head to the reservoir promenade in Olivebridge, NY, you’ll be treated to a paved and flat route that’s great for jogging and running. This portion of the trail is 2.8 miles (4.5 kilometers) long and hugs the southern shore of the reservoir, with great views of the Catskill Mountains looming in the distance. You may even spot a bald eagle!

Overlook Mountain Wild Forest

One of the most popular trails in Ulster County is Overlook Mountain, which is in the town of Woodstock. Free to the public, this unique spot offers hikers an opportunity to explore a historic fire tower, mountain house ruins, and awe-inspiring views of the Hudson River Valley and the Catskill Mountains. According to New York state’s Department of Environmental Conservation, on a clear day, you can see five states from the tower’s top at an elevation of 3,140 feet (957 meters). There are several different trails for any level of experience, from the more advanced Overlook Mountain Spur Trail, or the more leisurely Meads Meadow and Overloop trails.

Eat and Drink Locally in Ulster County

Ulster County offers plenty of options when it comes to dining, including local digs and world-class restaurants.


In New Paltz, check out casual local restaurant Huckleberry for a great space indoors and outdoors which features a yummy American eclectic menu. They have a range of cocktails and delicious donuts for dessert. Nearby in Gardiner, Mountain Brauhaus Restaurant is a family-run restaurant featuring authentic German cuisines like schnitzels and sausages. They source local meats and produce and, as can be guessed, have plenty of beer and drink options.

Up in Kingston, check out Hotel Kinsley’s restaurant for New American classics. Like the hotel, this place has a historic, swanky vibe. Main entrees include fish, chicken, and duck meals, with a yummy brunch menu and plenty of drink options. If you’re feeling Italian while in Woodstock, check out Cucina, opened by Chef Gianni Scappin and Lois Freedman in 2006, and situated in a restored and rambling 19th-century farmhouse. The signature menu is contemporary Italian based on seasonal and local ingredients, with large 24-seat communal options to eat with friends and more intimate spaces.

image courtesy: Mountain Brauhaus Restaurant-min

Farmer’s Markets

Another avenue for great food in this region is to check out local farms and bakeries. Farmer’s markets, stands, and shops across the county offer a variety of fresh produce and organically grown products perfect for a picnic. Saunderskill Farms in Accord has been around for over 300 years and is supported by 12 generations of the Schoonmakers family. It offers fresh produce grown from their fields as well as items from local vendors and farmers. You can grab coffee, breakfast, soups, sandwiches, and pre-made meals. If you’re looking for something sweet, Damn Good Honey Farm, nearby in Wawarsing, NY, offers sustainably-grown produce, honey, soap, and other hive products. Finally, check out Kelder’s Farm in Kerhonkson. This farm features pick-your-own fruits and vegetables and the world’s Largest Garden Gnome (seriously, they’re in the Guinness Book of World Records).

Breweries and Wineries

Rounding out our list of food and drinks are the region’s plentiful brewpubs, wineries, and taverns. In New Paltz, check out Robibero Vineyards, a 42-acre (17-hectare) family-owned boutique winery. Quantities are extremely limited due to their hand-crafted quality and sell almost exclusively in their tasting rooms and website. They also have fine cheese and wood-fired pizzas to eat. Nearby in Accord is Arrowood Farms, a beautiful sustainably-minded farm brewery, distillery, and dining destination. Their beer is brewed with ingredients grown on-site, and they support farm communities by locally sourcing their food and drink ingredients. They have great outdoor seating during the warmer months and are available to host events as well. They also have live chickens and cornhole to play!

If you’re more north in Kingston, try Stockade Tavern, located in the Senate House State Historic Site. Paul Maloney and Giovanna “Jenny” Vis are the owners of this classy watering hole set in a former Singer sewing machine repair shop. They are talented mixologists with plenty of cocktails and mocktails to choose from. And finally, if you’re in Woodstock, check out Woodstock Brewing, a brewery founded by two friends in their garage that is now a 15-barrel brewery. Relax in the indoor and outdoor seating environment, play Jenga, enjoy their beers on tap, and a food menu that includes appetizers, salads, soups, tacos, and sandwiches.

Looking to explore a different side of NYC once you’re back in the city? Check out Around the World in New York City: A Neighborhood Itinerary