By: @pretzelsinparadise
Come with us and our dogs on a weekend getaway to Ulster County exploring hidden history, art and music culture and all of the best things to do in Woodstock, Saugerties and New Paltz.
Day 1: Arrival in Woodstock
Just two hours from New York City, we arrived at our home base, the dog-friendly Woodstock Way. It is consciously built overlooking waterfalls and a stream and centrally located just off the main streets of Woodstock, walking distance to all the shops, food spots and theaters. Your stay includes free coffee and snacks daily, and this isn’t your typical k-cup coffee—we are still dreaming of the pistachio lattes.
After giving our baby daughter Summer a tour of the room, we explored the local shops along Tinker Street and watched live music in the square.
At night, we headed to the legendary Bearsville Theater for a concert! The historic compound includes a theater, recording studio and restaurants. The theater was originally built to showcase now iconic talent such as Bobby Dylan and Janis Joplin to music executives in an intimate state-of-the art acoustical experience. Today Bearsville is open to the public, hosting artists from around the globe both in their theatre and scenic outdoor venue. The studio is still active as well—The Lumineers even recorded their latest album there. This place keeps the spirit of Woodstock alive.
Day 2: Saugerties
The next morning we grabbed stuffed bagels at Moonrise and then headed for Saugerties. Our first stop was Opus 40, home to 60+ acres of property that includes hiking trails, a museum and most notably 6.5 acres of earthwork sculpture. Originally an abandoned bluestone quarry, Opus 40 became Harvey Fite’s life’s work to sculpt the rubble that had been left behind into terraces, ramps and walkways, all done by hand. Today his sculpture is also enjoyed as the stage to sunset concerts on Fridays in front of the gorgeous Overlook Mountain backdrop. It’s a beautiful example of how art and nature can come together in a sustainable way.
We then made our way to the main part of town for breakfast at Olsen and Company and visited the dog-friendly bookstore cafe, Inquiring Minds. Many of the buildings in Saugerties date back to the 1800s and there is even a lighthouse. The street’s history and development came to be by the shift in focus from the Hudson River to its role in the Revolutionary War and the Industrial Revolution to today.
For dinner, we headed back to Woodstock to Good Night. Walking distance from our hotel, this pan-Asian cuisine with a modern twist is focused on the love of the family meal and was the perfect cap to our great night.
Day 3: New Paltz
On our way home, we first stopped at Black Creek Preserve for a great dog-friendly hike. We clearly worked up an appetite and indulged at Lola’s Cafe in New Paltz, and then headed to Historic Huguenot Street, one of the oldest continuously inhabited streets in America, with seven original 18th-century stone houses. We actually know descendants of the Hasbrouck house! We drove by the 138-year-old Ann Oliver House, originally owned by a free black woman in New Paltz in the 1800s. It is currently under renovation and will be open to the public in 2026.
Our last stop was for some treats for the road at Lagusta’s Luscious where everything they make is ethical, small-batch and vegan.
Ulster County is full of so much hidden history, culture, and sustainable efforts, and we barely scratched the surface. Be sure to save the itinerary for your next trip!
