New York's 'Hippest Little Town You've Never Heard Of' Boasts Scenic Trails And Laid-Back Vibes

New York's Hudson Valley region is full of charming small towns, from this one locals call "the village" to this city with a vibrant downtown on the Delaware River. If you're exploring the valley, don't miss New York's "hippest little town you've never heard of" — Rosendale. With a population of under 6,000 people, Rosendale is located in Ulster County, around a two-hour drive from NYC. You can also take the Trailways bus from NYC directly to Rosendale or take an Amtrak train to Poughkeepsie station and then either call a rideshare or take a bus.

With scenic hiking trails and a laid-back, walkable downtown, Rosendale draws weekend visitors looking to escape the hustle and bustle of the big city. Once nicknamed "the hippest little town you've never heard of," Rosendale is now making a name for itself with a thriving arts scene and a creative population. "The town has become more popular," one Rosendale resident told Hudson Valley magazine in 2023. "There's a lot of fresh energy and young creatives, and it's really encouraging to see Rosendale thriving as a new generation takes over." One of those creatives is The Wing and Six Bells founder Audrey Gelman, who opened the Six Bells Countryside Inn and accompanying shop and restaurant in Rosendale in 2025. 

Nestled between Rondout Creek and Joppenbergh Mountain, Rosendale offers plenty of opportunities to explore the outdoors. Ulster County's Wallkill Valley Rail Trail passes through Rosendale over the stunning 940-foot Rosendale Trestle, a former railroad bridge-turned-walkway. Hikers, cyclists, and horseback riders from all over the region love to travel this path.

Then there are the hiking trails on the nearly-500-foot-tall Joppenbergh Mountain, offering stunning views of Rondout Creek, the Rosendale Trestle, and the charming downtown area. Leaf peepers flock to this area to watch the changing leaves (this fall foliage map shows exactly when to see peak color across the United States). One Google reviewer calls the mountain a "beautiful place to go to refresh and renew your body, mind, and spirit," adding, "I was here during the fall season when the leaves were dripping with a rich, deep amber and gold, which made my experience all the more exhilarating!" Hikers can also explore Rosendale's cement manufacturing history via the Lime Kiln Trail and Widow Jane Mine Trail. Both trails take you through local forests and into small mines. The Widow Jane Mine sometimes hosts live music performances and other local events; it can seat up to 500 people.

Rosendale's walkable and laidback downtown is home to a thriving arts community. The Rosendale Theater, a historic venue originally constructed as a casino in 1905, is one of the town's most recognizable landmarks. Today, it hosts live music and theater performances as well as both modern and classic film screenings. One TripAdvisor reviewer writes that it "feels like you're stepping back in time when you enter this theater." Rosendale is also home to the Redwing Blackbird Theater, an activist puppet theater with larger-than-life puppets.

Downtown, you can browse local boutiques, including independent bookstore Postmark Books; vintage clothing stores Soiled Doves and Clubhouse Vintage; and handcrafted gifts store Visions of Tibet. Popular local eateries include cheese shop and restaurant The Big Cheese, with a Mediterranean-inspired menu; the Garden Shop, with Arabic cuisine and an eclectic outdoor garden; and Soy, serving Japanese home cooking.

Throughout the year, Rosendale hosts several festivals, such as the Rosendale International Pickle Festival. Each October, thousands of pickle fans come to Rosendale to eat pickles (as well as other foods) and participate in events like a home pickling contest and a "Pickle Triathlon," featuring a pickle eating contest, pickle juice drinking, and a pickle toss. It's kind of a big dill.