If you want to check out Long Island’s North Fork, Greenport is an excellent home base—and has plenty of charms of its own. The town is known for having some of the North Fork’s best restaurants, including American Beech, a new American spot that does double-duty as a small, but lovely, hotel. Brix & Rye and Greenport Harbor are two excellent options for those seeking quality cocktails or craft beers, respectively. And, of course, there are beaches where you can kick back and relax. There’s also a ferry that takes folks to Shelter Island, should you want to check that out on your trip.

Not to be confused with Long Island’s Cold Spring Harbor, this town on the Hudson Metro-North line has a main street that feels like something out of a postcard. The locals love the town so much they stick its name everywhere: Get the hat trick by picking up organic skincare products at Cold Spring Apothecary, home goods and jewelry at Cold Spring General Store, and lunch at Cold Spring Depot, which is along the train tracks—ask for an outdoor seat if you want to watch the trains go whizzing by. Bonus: On weekends, a regional trolley picks up downtown and drops you off in front of Boscobel, the restored 19th-century mansion in Garrison.

Thanks to its location on the banks of the Hudson River, there's a lot of nautical history in Kingston. It's home to both the Hudson River Maritime Museum, which hosts exhibits and leads tours about the area, as well as the quaint and Instagrammable Rondout Lighthouse. But Kingston also has the sort of hip shops and restaurants that wouldn't feel out of place in, say, Brooklyn—spots like Clove & Creek, with its selection of home goods and accessories, or Brunette, a wine bar opened in 2015 by two Queens residents who fell in love with the town.

This hip hamlet along the Hudson River has become one of the better-known spots for New York City daytrippers, and for good reason: It has an abundance of cute shops, good restaurants, and cultural attractions, all packed into a relatively walkable two square miles of land. Spend some time window-shopping on Warren Street, the town’s main drag, or catch a show at Basilica Hudson, a repurposed factory turned concert venue close to the river. The Rivertown Lodge, located further inland, is a stylish spot to spend a night.

The town of Catskill, situated between the Hudson River and the mountain range that gives it its name, is home to Cedar Grove, the home of American painter Thomas Cole. Visit today and you’ll see the studio where he created some of his most enduring works, as well as the landscapes that inspired him. But that’s not the only reason that arts aficionados should plan a trip to Catskill; the town is a bustling creative hub, with a bevy of galleries and shops lining its charming Main Street. (Check out the Village Common for locally produced candles and home goods, or Open Studio, a gallery-cum-studio space owned by two local artists.)

For winter sports fiends, the town of Hunter—with its proximity to Hunter Mountain, one of the region’s best resorts—is an excellent place to spend a long weekend. There’s skiing and snowboarding for all skill levels, along with other cold-weather activities like snow tubing. To stay, there’s Scribner’s Catskill Lodge, a once-derelict inn that was renovated a few years back, keeping the midcentury bones while adding a dash of 21st-century cool.

Despite its college-town reputation, there's plenty to do in Princeton even if you're not a student. Princeton University Art Museum on the Ivy League campus is a must-visit for its diverse collection of artwork, while colonial artifacts can be seen on a tour of the Morven Museum & Garden. Enjoy homemade ice cream from one of the two locations of Thomas Sweet before winding down with a leisurely walk on the Towpath trail along Lake Carnegie. If you're planning a visit on a weekend, Princeton Tour Company offers two-hour tours showing off highlights of both the university and the town itself.

Ridgefield is a thriving arts community with institutions like The Aldrich Contemporary Art Museum, started from late fashion designer Larry Aldrich’s private collection. The Ridgefield Playhouse is a movie theater/performing arts center that’s played host to acts like comedian Marc Maron and musician Loretta Lynn, while the Ridgefield Theater Barn is a playhouse located in—you guessed it—a big, red converted dairy barn. For those who aren't artistically inclined, the Keeler Tavern Museum is dedicated to the area’s Revolutionary War history. Guests can even see a cannonball fired by the British still embedded in the tavern’s wall.

New England maritime history is center stage in Mystic, where the Charles W. Morgan, the country’s oldest surviving whaleship, is docked at the Mystic Seaport. The site of a recreated 19th-century seafaring village, the seaport shows off big ships and offers exhibitions on lighthouses, figureheads, and other maritime objects. But if you know the town, it may be for Mystic Pizza, the pizzeria made famous by the 1988 Julia Roberts flick. And no visit to the town is complete without enjoying scoops from Mystic Drawbridge Ice Cream while watching boats pass under the drawbridge.