New York City is among the greatest cities in the world and is the cultural and economic epicenter of the East Coast. Although the city always has something exciting, it is also surrounded by natural beauty and picture-perfect small towns that make perfect weekend getaways. Sometimes the best memories are waiting to be made on adventures! In the name of Exploration, we've found 20 incredible weekend trip destinations within driving distance of New York City.
A mixture of seaside, countryside and mountaintop destinations, these towns have something for everyone. Whether you want to ogle at art museums, stroll through gardens, hike up mountains, swim in waterfalls, relax at outdoor concerts or eat your way through a new town, we have you covered.
This article is chock-full of local suggestions for what to do, where to eat, and where to stay to make the best of your weekends and explore the beauty of the Northeast. Get going!
20 Hudson, New York
A picturesque town built on the Eastern bank of the Hudson River, Hudson, NY is just under a two-hour train ride away from Manhattan.
The historic town is full of beautiful architecture, and many of the old homes have been lovingly restored and even turned into businesses.
Take a walk down Warren Street, which spans more than ten blocks packed with small-town artistry. In the morning, visit Cafe Le Perche for a fresh croissant before you dive into the wealth of impeccably curated antique shops. Visit Le Gamin Country for lunch, and catch an afternoon class at Sadhana Yoga. For dinner, Mexican Radio is the hottest spot around. To stay, choose from any number of the gorgeous B&Bs set up plushly redone mid-19th-century homes, including the Croff House and Hudson City Bed & Breakfast.
19 Beacon, New York
Beacon, NY is a mid-sized town in the lush Hudson Valley, built close to the Hudson River. Once a manufacturing town, the location is close enough to New York (about an hour 15 by train) that some people commute, resulting in a slightly larger town but with the same charming scene. Although you could make it a day trip, Beacon is an ideal weekend spot. Stay at the Roundhouse, an upscale redone industrial space set on the Beacon River with a waterfall view. Within walking distance is the Mount Beacon trail, a pretty intense hike with an incredible view of the Hudson River as a reward. Also, a must-see is the art museum DIA, which features large-scale modern art installations (pictured).
18 Windham, New York
A charming town settled high in the Catskill Mountains, Windham is about a two and a half hour drive from New York City.
Although most popular in the winter for its family-friendly ski mountain, Windham is perhaps even more beautiful in the summer and fall.
Lush and verdant vegetation frames the quaint town, where shops and restaurants line the aptly named Main Street. Visit the Windham Spa for a luxe treatment with handmade products, and take a stroll around the scenic Windham Path. Stop in at Ze Windham Wine Bar for an evening drink, or visit Bistro Brie & Bordeaux for a fuller meal. Finally, sleep under the stars in your own tiny A-frame cabin in the woods at the newly opened Eastwind resort (pictured).
17 Woodstock, New York
Woodstock, New York is just under a two-hour drive from New York City. The famous little town lives in understated glory and makes a perfect good-vibes only getaway. Chock full of yoga studios and shops of all kinds, the character of this town is what keeps drawing visitors. Head to Oriole 9 for a sit-down lunch, or Bread Alone bakery for a quick soup or sandwich. Upstate Film Theatre plays all of the art and foreign films you've been meaning to see, and the local art galleries will keep you entertained for hours. For dinner, the Bear restaurant in nearby Bearsville serves excellent food situated right alongside a bubbling stream (pictured) and hosts great musical acts next door in the Bearsville Theatre.
16 Narragansett, Rhode Island
The quintessential beach town, Narragansett, Rhode Island is a top weekend destination.
The pristine beaches touch the Atlantic Ocean, fully away from the Long Island Sound, and are numerous, including Scarborough, Roger Wheeler, and East Matunuck.
The town's star eatery Crazy Burger is a BYOB burger joint with Vegan options and indoor-outdoor seating. If you aren't feeling burgers, try the Clam Cakes at Aunt Carrie's, where you can try the Rhode Island state delicacy made fresh by the descendants of their creator. If you can, snag a room at the Break hotel; the 16 large guestrooms have tons of retro-chic appeal and share a year-round heated saltwater pool.
15 Newport, Rhode Island
Just a bit farther than Narragansett is the historic island town of Newport. The fun, youthful beach town has a thriving nightlife scene and more quirky gift shops and upscale boutiques than you'll be able to visit. Historically the choice New England getaway of the mega-wealthy, be sure to tour some of the numerous mansions that line the coast, belonging to significant families throughout time. The most grandiose is The Breakers, the summer "cottage" built by the Vanderbilt family in the 1890s. Although the dining options are numerous, we recommend Midtown Oyster Bar for dinner or a large lunch (pictured), and Salt Water Harbourside Dining for an outdoor brunch.
14 Sag Harbor, Long Island
On the North side of the coast of Long Island is the least pretentious of the Hamptons towns, Sag Harbor.
With as much charm and beauty as the other towns, Sag Harbor is kid-friendly and less stuffy than some of the other famed towns of the Hamptons.
Catch a class at Yoga Shanti, and pop into LT Burger (pictured) for the best milkshake of your life. Do the classic Hamptons thing and rent a sailboat (and sailing instructor, of course) or head to the rocky shore for a quick dip. Also worth a visit is the Whaling & Historical Museum. When you're done for the day, enjoy a great meal on the water at the Dock House.
13 Shelter Island, Long Island
Just above Sag Harbor along the picturesque North Fork of Long Island is Shelter Island. Just a ferry ride away, this stunning place is said to feel like a different place and time. Away from the hustle-and-bustle of the rest of Long Island, Shelter Island is serene and tranquil. Locals recommend Stars cafe or the Islander for a classic continental breakfast, and the Salt Waterfront Bar and Grill for a classic and creative seafood menu and incredible views. The most popular place for a swim is Crescent Beach, just steps away from the Shelter Island House hotel. With a third of the island saved in Mashomack Preserve, the peaceful nature of this place won't be disturbed any time soon.
12 Saratoga Springs, New York
Saratoga Springs is an Upstate New York town so famous that Disney World in Orlando has a resort themed after it.
The chic, elegant Americana luxury that is uniform in Saratoga is a welcome respite from and foil to the town's surrounding wilderness.
A three and a half hour drive up from NYC, Saratoga is settled in the midst of intense natural beauty, offering an available mix of both. Hike up the Geyser Creek Trail to admire the natural mineral springs and active geyser, and then stop in town for lunch at Sperry's. Definitely pay homage to the town's fame and history with a visit to the Race Track before you go!
11 Cooperstown, New York
Known for being home to the Baseball Hall of Fame (and the birthplace of the sport, according to legend), Cooperstown is worth a visit even to the sport-adverse. The little brick town has all of the charm of the country, plus the postcard-worthy beauty of Glimmerglass Lake. Spend the day out on a boat, or swimming along the pebbly shore. Visit the Fenimore Art Museum, or the Farmer's Museum. Cap your stay off with a trip to the prolific Brewery Ommegang, with either a tour and a flight of beer over dinner in their on-site restaurant, or a fabulous concert in their large-scale outdoor venue. Stay at the Otsega Resort Hotel, pictured here, and take in one of these sunsets with your own eyes!
10 Stonington, Connecticut
Located along the easternmost coast of Connecticut is the picturesque town of Stonnington.
Traditional saltbox houses line right up to the coast, flanked with hydrangeas and sandy paths.
Visit the locally sourced Stonnington Farmers market Saturday morning, and then get a casual breakfast at Noah's Restaurant. Enjoy the coastal views along the Stonnington Harbor nature walk, and then visit the Old Lighthouse Museum, where you can climb the light tower and enjoy a three-state view from the top. For dinner, hit Dogwatch for casual seaside dining, or the Water Street Cafe's oyster bar. Also, don't forget to get to DuBois beach for a swim!
9 Stowe, Vermont
Nestled at the foot of Mount Mansfield, the tallest peak in Vermont, is the picturesque town of Stowe, Vermont. Known for skiing, the area is also a gorgeous destination in all seasons. If you're outdoorsy, enjoy the beautiful Smuggler's Notch, an area of complete wilderness preserved in the Mount Mansfield State Forest, visit the stunning Moss Glenn Falls, or if you're super adventurous, hike Mount Mansfield itself. Enjoy swimming at one of the many resort's pools or nearby lakesides, or kayak along the Waterbury Reservoir. Visit the many local distilleries and spas if you're feeling flush, and retire to the luxurious resort of your choice after a jam-packed day of adventure.
8 Salem, Massachusetts
A town steeped in history and mystery, Salem, Mass, is the home of the infamous Salem Witch Trials.
The town has done an excellent job of keeping the story of the 1692 witch trials alive, with landmarks and museums galore.
However, the town itself is also a worthy modern-day destination. Visit the Peabody-Essex Museum to appreciate it's global collection of art and artifacts, and visit the Salem Willows park to ride the carousel and hit the arcade. Drive out to Winter Island to visit the photogenic lighthouse and take in the Massachusetts coast. Get to the Howling Wolf Taqueria for some from-scratch Mexican food, or head to Finz for an incredible meal on the water!
7 Mystic, Connecticut
Mystic, Connecticut is a town "devoted to all things Maritime." The family-friendly town is home to Mystic Seaport, a recreation of a 19th-century seafaring village, as well as the Mystic Aquarium, home to beluga whales, seals, and dolphins. The active Mystic Art Association fosters the town's thriving gallery and studio scene, featuring local artists. Not to be missed is Mystic Pizza, where you can have a slice in the place made famous by the Julia Roberts movie of the same name. Adults can enjoy the nearby Foxwoods and Mohegan Sun casino complexes, and the whole family can retire together to one of the area's many highly rated hotels.
6 Hunter, New York
A Catskill Mountain ski town, Hunter, NY is just under a 2.5-hour drive from New York City.
Whether you come in the winter to enjoy skiing and snowboarding at the mountain, or in the summer to soak up some mountaintop sunshine, Hunter is a youthful and fun area.
Visit North and South Lake state park for a swim along the sandy beaches or a hike to Artist's Point, or head down to Kaaterskill Falls for a dip at the bottom of the three-tiered waterfall. Have lunch or dinner at Prospect restaurant in the newly renovated Scribner's Lodge (pictured), or stay in one of their cozy guest suites. Enjoy the local fare, or pop over to neighboring Windham for a bite!
5 Greenwich, Connecticut
Greenwich, Connecticut is famous for having the enormous mansions of NYC's wealthiest commuters. The beautiful brick town is surrounded with massive estates, home to everyone from famous directors to fortune 500 CEOs. Although people living in Greenwich might not consider it a vacation destination, the pristine little town is definitely worth a weekend trip for the rest of us! Visit famous architect Philip Johnson's iconic Glass House, or stroll through the stunning nearby Donald M. Kendall Sculpture Gardens. If you can swing it, a stay at the Hyatt Regency Greenwich means a visit to the gazebo bar underneath the enormous enclosed glass terrarium.
4 Lenox, Massachusetts
Known as a hotspot for culture-driven travel, Lenox in the Berkshires, Mass, offers something for everyone.
Open air concerts at the nearby Tanglewood Music Center draw a massive 35,000 visitors annually, and the area's agricultural roots shine through in local farm-grown cuisine.
Stay in an iconic property like Wheatleigh, in 16th-century palazzo style, or at the famous luxury wellness retreat Canyon Ranch. Browse the local boutiques, and dine at the cozy Nudel for locally-sourced delicacies. Hilltop Orchards offers the ultimate farm experience, and there is plenty of local hiking (or snowshoeing!). Finally, you have to stay for a concert at Tanglewood with a picnic under the stars.
3 Cape May, New Jersey
At the tip of Southern New Jersey's Cape May Penninsula is the fruity-colored and sun-washed city of Cape May. Known for its grand Victorian houses painted bold and beautiful colors, Cape May (which calls itself America's Oldest Seaside Resort) is a town full of history and dotted with local museums. The bustling downtown features the Washington Street Mall, three pedestrian-only blocks lined with shops and restaurants. Visit the iconic Cape May lighthouse, and get some rays one the scenic Sunset Beach. Go to Morey's Piers for a 6-block long classic beachfront amusement park that the whole family will love!
2 Montauk, Long Island
At the very tip of Long Island is Montauk, also called "the End," or even, "the End of the World."
Despite this melodramatic nickname, Montauk is a cheery and fun town.
Beaches like Ditch Plains are home to the strong Atlantic Surf, and at the Montauk Point State Park, you can see where the Long Island Sound and the Atlantic Ocean meet. The beautiful area was once home to a military base during WWII, and Camp Hero State Park still has bunkers and a radar tower. The Montauk Point lighthouse has an on-site museum open to visitors. The point is also home to modern-day luxury and amenities; stay at Gurney's Spa and Resort (pictured) to enjoy shaded day beds on the private beach!
1 Annandale-On-Hudson, New York
Annandale-On-Hudson is a charming hamlet of Red Hook, NY, across the Hudson River from Kingston. Home to the renowned Bard College, this little town is full of culture and beauty. Visit the Richard B. Fischer Center For the Performing Arts on campus, a Frank Gehry designed venue that hosts world-class musicians and dancers. Enjoy a picnic lunch at any one of the numerous gardens overlooking the Hudson River before heading to Montgomery Place to tour the 380-acre 200-year old architectural landmark designed by Alexander Jackson Davis. Visit the nearby Catskill Animal Sanctuary or hike through the Falling Waters Preserve.