Things To Do
Beacon
Beacon’s picturesque Main Street is lined with boutique shops, galleries, and a diverse array of dining options, reflecting the city’s blend of historic charm and modern culture. Known for its vibrant arts scene, Beacon is home to the renowned Dia:Beacon museum, which showcases an impressive collection of contemporary art in a repurposed factory space. There is also a direct 1hr 40min train to NYC from Beacon train station. For coffee/breakfast: Kitchen + Coffee, The Beacon Daily, Beacon Bread Company, Big Mouth Coffee Roasters, Matcha Thomas; also try vegan donuts at Peaceful Provisions. For lunch/dinner: Meyers Old Dutch, Melzingah Tap House, Coopers, Town Crier Cafe, Ziatun, Quinn’s. For drinks/breweries: Wonderbar Beacon, Hudson Valley Brewery, Industrial Arts Brewing.
Fishkill
Rich in history, Fishkill played a significant role during the Revolutionary War and now offers a blend of historical sites and modern amenities. Check out Il Figlio Italian restaurant, Dutchess Biercafe, and La Sorella for brunch and breakfast, and Hot Stuff for coffee!
Wappingers Falls
Wappingers Falls, NY is a small, lively village that blends historic charm with a growing, family-friendly community vibe. It’s also where me and Conor live! It’s known for its walkable downtown, local shops, parks, and a tight-knit atmosphere. The area is seeing a steady wave of revitalization, with new restaurants, cafes, and small businesses popping up. For breakfast/coffee try Normas Village Cafe. For lunch/dinner try Casa Ortega, Cafe con Leche, Lopburi Thai, Patsys Pizzeria, Braised Pies (a British pie shop!). For drinks: County Fare pub, di’Vine wine bar, day&nite lounge. Sneak a sweet treat at Quincy’s Candy Shop or ice cream at the Village Creamery! Take a stroll around Mesier Park and the Mesier Homestead and Museum.
Cold Spring
Cold Spring, NY is known for its historic Main Street, coffee shops, antique shops, and scenic river views. It has a relaxed, artsy vibe with a strong sense of preservation and community. It’s walkable, cozy, and full of character. For breakfast/coffee try Cozy Corner cafe, Citrine Cafe, Angie’s bake shop. For dinner: J Murphy’s on Main, Le Bouchon.
Rhinebeck
Rhinebeck has been the scene of many historic events, and comprises one of the largest historic districts in the United States. Rhinebeck offers shopping, dining, arts and entertainment. The nearby Amtrak station in Rhinecliff (and the Metro North station in Poughkeepsie) offers access from New York City and beyond. Check out Bread Alone, Abas Falafel, and Samuel's Sweet Shop!
Woodstock
Cute mountain town which is famous for its 60s Peace & Love Era with the addition of many new restaurants/bars! Fun fact: the Woodstock concert did not actually happen in Woodstock due to a last minute dispute with a farmer on his land. It happened in Bethel Woods almost 1.5 hrs drive away! Check out Goodnight, Bread Alone, SILVIA, Small Talk.
Kingston
Kingston was New York state's first capital! Fun city with great new bars and restaurants, many coming straight from NYC! For drinks: Westkill Supply, Keegan Ales, Lone Wolf; for coffee/snacks: Rough Draft Coffee & Books; for dinner: Front Street Tavern, Mirador, Sorry Charlie, Chleo, Ollie's Slice Shop.
Hudson
Hudson was the first city to be incorporated after the thirteen colonies became the United States! Lots of room to stroll and stop into one of the many breweries, coffee shops or antique shops! Check out Hudson Roastery, Return Brewing, and the Henry Hudson Riverfront Park.
Hudson Valley Brewery
Brewery at the end of Main Street Beacon known for its sour beers. Newly renovated indoor/outdoor space with gorgeous views overlooking Mt Beacon!
Arrowood Farms
Farm brewery with their own range of craft beers, ciders and great food!
Westwind Orchard
Just up the road from Arrowwood! Great to combine into one visit. Good pizzas and fresh cider!
Woodstock Brewing
Great brewery to visit if you're exploring the Catskills mountain range. Great selection of vegan/veggie options and beer!
Phoenicia Diner
Right next to Woodstock brewery and the Ashokan rail trail, lots of great options!
Walkway Over the Hudson
The Walkway over the Hudson is bridge spanning the Hudson River between Poughkeepsie, New York, on the east bank and Highland, New York, on the west bank. Built as a double track railroad bridge, it was completed on January 1, 1889, and formed part of the Maybrook Railroad Line of the New York, New Haven and Hartford Railroad. It was taken out of service on May 8, 1974 and reopened on October 3, 2009, as a pedestrian walkway as part of the new Walkway Over the Hudson State Historic Park.
Mount Beacon Trailhead
Great hike to see views of the Hudson River!
Long Dock Park
Riverfront park with picnic benches and walking/biking trails along the Hudson River. Kayaks and paddleboards also available for rent!
Ashokan Rail Trail- Boiceville Bridge Trailhead
Flat trail next to the Ashokan reservoir. Tip: rent a bike from Overlook Bicycles right next to the trail head to see more of the trail!
Minnewaska State Park Preserve
Minnewaska State Park Preserve is situated on the dramatic Shawangunk Mountain ridge, which rises more than 2,000 feet above sea level and is surrounded by rugged, rocky terrain. The park features numerous waterfalls, three crystalline sky lakes, dense hardwood forests, cliffs and ledges opening to beautiful views, clear streams cut into valleys, 35 miles of carriage roads and 50 miles of footpaths on which to bike, walk, hike and enjoy.
Overlook Mountain Trail - Fire Tower Spir
We went here on one of our first hikes together! Its a great hike to combine with a visit to Woodstock.
Indian Head Mountain Trail
Conor proposed at the lookout point on this hike! It's our favourite hike in the Catskills! Expect to spend at least 4-5 hours on this trail, steep climbs w/some scrambling. Recommend wearing proper hiking boots and intermediate hiking experience.
DuBois Farms
Lovely farm known for its seasonal U-Pick and year-round treats! Apple picking season in the Hudson Valley starts in late August!
Mills Mansion
Staatsburgh State Historic Site was the elegant country home of Ogden Mills and his wife Ruth Livingston Mills. Overlooking the Hudson River and the Catskill Mountains, Staatsburgh is a fine example of a great estate built by America's financial and industrial leaders during the Gilded Age (1876 - 1917). Today the elegant mansion, restored to its turn-of-the-century appearance, is open for tours and the house and grounds offer special events throughout the year.
Vanderbilt Mansion National Historic Site
Historically known as Hyde Park, the Vanderbilt Mansion National Historic Site is one of the area's oldest Hudson River estates. Take a walk around the grounds of the historic mansion or grab tickets to tour the Vanderbilt Mansion itself.