The historic town of Roxbury is fun to walk or take in the foliage on a train ride with the Delaware and Ulster Railroad, which departs from a historic depot in Roxbury. Mini day trips from the area include Cooperstown and the Baseball Hall of Fame, an hour away.
2. Think Big! A Tiny House Resort – South Cairo, New York
New Yorkers are used to small-space living, but you’ve never seen anything like this tiny house resort. There are 15 tiny houses on-site, each sleeping 2-7 people. Each home has a flush toilet (no small feat in the tiny house world!) and a working kitchen, plus an outdoor porch with a gas grill and fire pit. Patrons are welcome to visit the flock of chickens to collect eggs for breakfast or harvest fresh veggies from the garden. More farm fun includes goats, bunnies, and ducks to interact with and enjoy. Looking for other entertainment? Hop in the heated pool, go for a hike or borrow a kayak to paddle your way along the streams. Nearby, you’ll find plenty of forestlands to explore, and if the snow flies early, you’re not too far from some of the region’s best skiing.
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Enjoy an Adirondacks hideout at Elk Lake. Photo courtesy of the lodge
3. Elk Lake Lodge — North Hudson, New York
If you’re seeking a digital detox, Elk Lake Lodge should be on your radar. This family-owned property is immersed in a 12,000-acre forest high in the Adirondacks. The lodge offers six small rooms and eight individual cabins of varying sizes. It presents a timeless retreat and opportunity to commune with nature with no televisions or cell phones to distract. Many activities revolve around the pristine Elk Lake with its 30 scattered islands and many coves and inlets to explore. Grab a kayak or canoe, jump in for a late-season swim, or fish for speckled trout. There are scores of hiking trails fringed with a rainbow assortment of leaves. Low-key activities include listening to the call of the loons, watching the leaves change colors next to the sparkling water, catching frogs, and helping to ring the dinner bell. Rates include a hearty breakfast and dinner, plus a packed lunch. Local ingredients are featured, and the fresh tastes should appeal to kids. Meals are served in the lodge overlooking Elk Lake, so you’ll dine with a view. Open seasonally through early October.
4. Legoland Hotel – Goshen, New York
Situated about 60 miles outside New York City in Goshen, the 150-acre park is the biggest Legoland yet. Geared toward ages 2-12, visitors can explore seven themed “lands” featuring more than 50 rides, attractions, and shows. You’ll be able to soar around the kingdom on the Dragon coaster, go for a spin at Lego City’s Driving School, shoot water cannons at pirates, hop aboard the Duplo Express, master the art of Spinjitsu at Ninja Training Camp, and lots more. Special seasonal events include a Brick-or-Treat Monster Party. After a day of theme park fun, you can stay in one of the 250 rooms at the Legoland Hotel, each with a separate kid’s sleeping area and cool Lego themes like Lego Pirates, Kingdom, Ninjago, and even Lego Friends. Aside from being within steps of the theme park, perks include an impressive free breakfast buffet daily, in-room scavenger hunts, plenty of bricks to build with, and more family-friendly entertainment.
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Take in the splendor of the season with a fall getaway to Mohonk Mountain House in New Paltz. Photo courtesy of the venue
5. Mohonk Mountain House – New Paltz, New York
This Victorian-style castle is an old-world resort with charming accommodations and stunning grounds year-round, especially during the fall, where foliage is at its best. Cozy guest rooms include fireplaces or rocking-chair balconies but no televisions, so it’s easy to unplug. There’s a kids club, myriad indoor and outdoor activities, an award-winning spa, and loads of entertainment options. The heated, indoor pool is a big draw for families. The striking resort overlooks Lake Mohonk and the Shawangunk Mountains and is loaded with old-fashioned charm. Parlors and porches, fireplaces, and libraries abound in this National Historic Landmark. Three meals a day are included. Prepare to feast with bountiful buffet tables, chef’s stations, small plates, and a children’s station marked by balloons. A stay here is not particularly budget-friendly, though keep an eye on its specials, including deals for kids to stay and eat FREE.
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Montauk is a beautiful fall destination and the crowds of summer are much lighter.
6. Gurney’s Resort – Montauk, New York
Montauk on Long Island’s East End is a perfect spot to enjoy the sand and water, even in the fall. You’ll also get the added benefit of fewer crowds. Stay at the elegant Gurney’s, the only four-season beachfront resort in the Hamptons. There are various rooms, suites, bungalows, and cottages to choose from, some with dramatic ocean views. Climb the Montauk Point Lighthouse, charter a boat, ride bikes, eat fresh seafood, or take a hike through one of Montauk’s state parks. No car, no problem: Montauk is accessible via the LIRR.
7. Whiteface Lodge – Lake Placid, New York
Fall is a great time to explore the beauty of Lake Placid, nestled in the Adirondack Mountains. Stay at the rustic Whiteface Lodge, which is great for families with a wide range of rooms and suites, many outfitted with common areas and kitchens. Whiteface Lodge offers many activities, including swimming, tennis, skating, hiking, games, and canoeing. You can also relax at its award-winning spa. Explore the town of Lake Placid, where the Olympic Museum is located, and Adirondack Park, the largest protected area on the US mainland.
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Build a fairy door and explore the Fairy Forest at The Emerson Resort and Spa. Photo courtesy of the resort
8. The Emerson Resort & Spa – Mount Tremper
Whether you opt for a room in the contemporarily styled Inn or stay in the log cabin-inspired Lodge, a trip to The Emerson is sure to please. Situated on 20 beautiful acres, the Catskill Mountains and Hudson Valley are at your doorstep. Located on the grounds you’ll find the World’s Largest Kaleidoscope, sure to delight curious kids. Outdoor enthusiasts can embark on a self-guided bird walk along the Ashokan Rail Trail, enjoy a guided walk along the grounds to learn more about the region’s history and wild inhabitants, and close out the day with s’mores at a community bonfire. Kids will delight in exploring the Emerson Fairy Woods and making their own fairy door to add to the collection. Find more attractions and special events on The Emerson website.
9. The Kartrite Resort – Montecito, New York
If you’re trying to hold onto summer for just a wee-bit longer, consider booking your weekend getaway near NYC at this Catskills property, which is home to the largest indoor water park in New York state. It’s home to 324 guest rooms, all of which are family-friendly suites and include perks like mini-fridges and microwaves, plus a stocked Keurig coffee bar. Some even have balconies overlooking the resort. As far as entertainment goes, it’s hard to beat the two-acre indoor water park. Its 80,000 square feet of attractions include everything from a heated indoor-outdoor pool to high-flying slides for thrill-seeking big kids, a Flowrider surf simulator, and Kartrite Island—the water play area with knee-deep water perfect for little ones. The lazy river is a hit all around! While water park tickets are included in your stay, there are tons of other indoor attractions for an extra fee.
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Bucks County, Pennsylvania, offers stunning fall foliage and plenty of history to explore. Photo by Reflections by Ruth/courtesy of Visit Bucks County
Fall Weekend Getaways in Pennsylvania
10. Black Bass Hotel – Lumberville, Pennsylvania
This hotel offers a selection of eight spacious suites and has some killer deals through the end of the year. History buffs can appreciate a visit here for many reasons. The hotel dates back to the 1740s and overlooks the Delaware River, sitting just 14 miles upstream from the spot of George Washington’s famed crossing. President Grover Cleveland was a frequent guest and has a suite named in his honor. Renovated about 10 years ago, care was taken to preserve the hotel’s history while providing modern creature comforts. Bucks County is home to plenty of family-friendly destinations, including the preschool-friendly Sesame Place, which is open on weekends in the fall. For less commercial seasonal fun, consider booking a ride on the New Hope Railroad. You’ll board a restored early-1900s train and enjoy a narrated ride through the countryside. If you prefer to seek scenery on your own, embark on a tour of the region’s covered bridges. Save time to stop by Peddler’s Village, where you can shop at more than 65 unique stores, grab snacks, and gape at its Scarecrow Village or participate in a scarecrow-making workshop.
11. Hotel Darby – Beach Lake
To label this a new-to-the-scene hotel a Pennsylvania weekend getaway feels a bit like a misnomer. While Hotel Darby is located on the banks of Delaware in Pennsylvania, it’s just across the river from the quaint Narrowsburg, New York. Hotel Darby’s well-appointed, mid-century modern rooms provide a great jumping-off point for recreation along the river and beyond. Hiking trails abound; you can enjoy bird-watching in the meadows on the 17-acre property or start a family tournament at the cornhole boards. Hit the water in a rented kayak or canoe, or drop a line and try your hand at catching dinner. Narrowsburg’s bustling main street beckons just a three-minute walk down the road.
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Skytop Lodge in the Poconos is full of fun, family-friendly fall activities. Photo courtesy of the lodge
12. Skytop Lodge – Poconos, Pennsylvania
The picturesque Poconos are chock-full of family fun. Whether it’s warm or cold out, there’s plenty to keep the kids busy. At the Skytop Lodge, choose from a room in the historic lodge or a cabin nearby, and take your pick of delicious dining options throughout your stay. Downstairs, there’s a game room with pingpong, mini golf, and arcade games for kids and adults alike. In the fall, enjoy nature walks, lawn games, and boating. Older kids (10 and up) can take advantage of the year-round TreeTop Adventure Course. The hotel offers swimming in any weather—there’s an indoor pool if it’s cold, and an outdoor pool if you come in warmer weather.
13. Camelback Resort – Tannersville
You may think of Camelback as wintertime destination thanks to its ski resort or a summertime hotspot because of its outdoor water park, but we are happy to report that there’s plenty of all-seasons fun to be had at this Poconos resort. We love its variety of hotel rooms and suites, multiple restaurants, plus activities indoors and out. In addition to the all-seasons indoor water park (included in your stay!), there’s always something going on in the lobby—and bonus—it’s usually FREE.
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For a quick New England getaway, consider a stay at The Delamar Southport. Photo by Jody Mercier
Fall Weekend Getaways in New England
14. Delamar – Southport, Connecticut
Southport is the sort of all-American town that brings to mind parades and ice cream cones. The cobblestone streets are lined with stately homes and charming shops, giving it a Norman Rockwell feel. It’s located on a swath of Connecticut shoreline around 90 minutes from Manhattan. The Long Island Sound’s water usually stays warm enough for a dip into early October, and the coastal influence means leaves change a bit later in the season than they do inland. The Delamar Southport is just minutes from the beach. It offers 44 rooms loaded with luxuries. A complimentary breakfast is one of its perfect perks. The on-site Artisan Restaurant features New England-inspired farm-to-table dining. The spa is top-notch, so try to sneak in a treatment. It’s pet-friendly, too. The hotel is just a short distance from the Maritime Aquarium in Norwalk and the Beardsley Zoo in Bridgeport.
15. The Whaler’s Inn – Mystic, Connecticut
You don’t have to go far from NYC to experience classic New England vibes. The Whaler’s Inn offers history and scenery in equal amounts in Mystic, Connecticut. Mystic is just a few hours by car from NYC and offers all the seaside views you crave. Get your timed-entry tickets for the not-to-be-missed Mystic Aquarium in advance. It has everything from seals to sea urchins and even an exhibit on dinosaurs! Continue your seaside-themed weekend with a snack at the Sea View Snack Bar, which offers low-key eats in a family-friendly environment. Take the family on a cruise by sailboat, motorboat, or steamboat, and wrap up the weekend with a visit to the Mystic Seaport Museum. This re-created 19th-century fishing village lets kids explore a variety of maritime trades. Want more ideas for your weekend getaway? We’ve got them here.
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After a day of adventure, lounge in your room at the Bluebird Sunapee. Photo by Jody Mercier
16. Bluebird Sunapee – Sunapee, New Hampshire
This reimagined roadside motel has all the charm of a boutique property at a budget-friendly price point that’s packed with family-friendly amenities. We loved the common areas here, which included a rec room stocked with board games, a kid-friendly arcade, and an indoor saltwater pool, plus outdoor fun like lawn games and a fire pit lit nightly for your s’more-making pleasure. Accommodations are cozy and comfortable with plush beds and homey touches. Book adjoining rooms if you have a larger family. While there’s no on-site restaurant, a collection of over-the-top vending machines serves hot food and the Salt Hill Pub Shanty is just across the parking lot and dishes up American comfort food classics, plus plenty of brews. A short walk away, find Mt. Sunapee State Park Beach where you can rent kayaks and go for a paddle. Prefer to see the water from a motor boat? Visit one of three Goodhue Boat Company outposts sprinkled along the shores and rent a boat. Hiking is abundant and the fall foliage in this region of New Hampshire is out of this world gorgeous. When the flakes fly, Mount Sunapee ski resort is just minutes away.
17. Hotel on North – Pittsfield, Massachussets
This character-filled boutique hotel is centrally located on Pittsfield’s main drag. Housed in a historic building, the recently remodeled property has been reimagined with the modern traveler in mind. No two rooms are alike, but each has plenty of charm and creature comforts. If you’ve got a Beauty and the Beast fan on your hands, see if the Library Suite, which sleeps four, is available. It’s home to an enchanting scene with 125 story-filled bookshelves and a moving ladder. Use Hotel on North as a jumping-off point to explore The Berkshires’ town, which offers tons of family-friendly things to do. We loved our visit to Herman Melville’s Arrowhead estate, were wowed by the natural beauty during a local hike and enjoyed plenty of delicious eats. Kid-friendly picks include Marketplace Cafe for a casual lunch and homemade desserts, King Kone for a larger-than-life frozen treat, and one of two dueling hot dog shacks steeped in local lore: Hot Dog Ranch and Teo’s. Work all those delicious calories off with a trek through The Boulders nature preserve to take in the changing colors of the towering forest or while cheering on the iconic Pittsfield Halloween parade.
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The Inn by the Sea lives up to its name with stunning ocean views. Photo courtesy of the resort
18. Inn by the Sea – Cape Elizabeth, Maine
Coastal Maine is peaceful in the fall, so if you’re considering a long weekend getaway that combines the best of town and country, add the Inn by the Sea to your list. This Cape Elizabeth hotel looks like a peaceful painting, yet it’s only a 15-minute drive from the hipster haven of Portland, which is brimming with top restaurants, shops, and family activities, including a children’s museum. The hotel’s location on Crescent Beach provides a private boardwalk that leads through a wildlife sanctuary to a mile of unspoiled sand where kids can build sandcastles and might even glimpse a seal or two. The view is enchanting in fall, with subtle touches of color blending with the seascape. The 61 contemporary rooms include spacious one- and two-bedroom suites and traditional rooms with fireplaces. Suites have fully equipped kitchens and sofa beds.
The inn offers family-friendly programming like family yoga and fire pits complete with s’mores bars. Visit the historic Portland Head Light, the oldest lighthouse in Maine, surrounded by space for kids to run and explore. The Inn’s Sea Glass restaurant offers a dining experience with an eco-emphasis on serving underutilized, yet delectable, Gulf of Maine seafood. If your children don’t care for fish, there’s a standard kids’ menu. The inn is also one of the most pet-friendly hotels anywhere, so bring the pooch for some canine pampering.
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Stay at the Woodstock Inn, then tour the area for farm fun, foliage, and wildlife. Photo by Sultry/Sulky/Silly/CC BY 2.0
19. Woodstock Inn – Woodstock, Vermont
Vermont is loaded with charming villages and covered bridges, but even in a state chock-full of quaint, Woodstock stands tall. Nestled in majestic mountains, it’s a top spot to view the fall foliage, which greets you around every bend. The Woodstock Inn is the essence of New England hospitality and a great jumping-off point for family fun in the area. The 142 spacious rooms and common areas are loaded with cozy touches. Complimentary bikes, large indoor and outdoor pools, and hiking trails provide hours of fun. Kelly Way Gardens, the resort’s on-site garden, provides a holistic food supply to the resort’s restaurants.
Don’t miss a visit to the Billings Farm & Museum. It’s a fully operational dairy farm where you can get up close with the cows. Educational programming is excellent, and hotel guests enjoy free visits. F.H. Gillingham & Sons is Woodstock’s general store, owned and operated by the same family since 1866. It sells an eclectic range of goods, many produced locally, but quality is the unifying factor. Kids also enjoy a trip to VINS Nature Center, a rehabilitation center for birds of prey, many of which are on display, that offers educational activities and even shows for kids, plus nature trails. On your way, stop to gawk at the majestic Quechee Gorge, which is sure to stun the whole family into silence (for a moment or two).
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Bike along the Norwottuck Rail Trail in Northampton, Massachusetts. Photo by Rusty Clark/CC BY 2.0
20. The Hotel Northampton – Northampton, Massachusetts
Hampshire County in Massachusetts is a blend of artsy villages, progressive college towns, and agricultural landscapes. Northampton is home to Smith College, where the garden-filled campus is great for a stroll, and a visit to the Smith College Museum of Art is worthwhile. The small art collection is impressive, but just as memorable are the museum’s decorative public bathrooms. Even if nature doesn’t call, don’t miss these bold, creative, functional works of art. The historic Hotel Northampton offers 106 guestrooms, gracious public spaces, and friendly service, all within walking distance from everything. Rent bikes at Northampton Bicycle and cycle the flat, 11-mile, car-free Norwottuck Rail Trail to Amherst. It’s fringed with a canopy of colorful fall leaves and is just right for most school-aged kids to handle at least a section. The trail offers many snack options along the way, including luscious ice cream at Maple Valley Milk Company and Farm Store.
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Glamp in the White Mountains of New Hampshire for the full fall effect. Photo courtesy of Huttopia Camping
21. Huttopia Camping – Albany, New Hampshire
Camp without sacrificing comfort in the White Mountains when you stay in glamping-style tents loaded with homey amenities. Huttopia, open seasonally until mid-October, is ideal if you want a low-stress camping experience. It provides kitchen supplies, bedding, and more. The Trapper’s Tent sleeps up to five on real mattresses and includes a bathroom. Book the Chalet, and you’ll stay in a two-bedroom wooden cabin that sleeps up to six and includes a kitchen and bath. Fish in the lake or take a nature hike. There are low-key organized activities for kids in summer, and a few sporadic ones continue into the fall. If you crave the 21st century, head to North Conway, just 10 miles away. We’ve got tons of family-friendly picks nearby in our roundup of 25 things to do in the White Mountains.
22. Smugglers’ Notch Resort – Stowe, Vermont
While popular for skiing, Smugglers’ Notch Resort is also an ideal vacation spot in the fall with so many outdoor adventures and special activities. The full-service resort publishes a guide, nearly 50 pages thick, chock full of things to do each season. Offerings include yoga, magic shows, sports, swimming, guided excursions of every ilk, and family movie screenings. Kids love to visit the Fun Zone, a kids’ activity center with games, bouncy castles, and other amusements—though plan your adventure soon. The Fun Zone is scheduled for a three-week closure in October. There’s also a similar space for teens. Also popular is the three-hour Zip Line Canopy Tour. If you’ve got spare time, the town of Stowe, also known as “Aspen of the East,” is close by and offers a ton of activities, sights, and places to visit.
A version of this story was published in 2017; Jody Mercier contributed additional reporting.
