There’s nothing like getting a little fresh air after a winter cooped up at home with the family. If the mountains are calling your name, read on as we tour guide you through the Berkshires, Catskills, and Poconos. Start rolling down those windows and get ready to revel in blissful mountain vibes.
Upscale R&R in the Berkshires
The minute you take those first exits into the Berkshires, the living just seems easier. The region, which spans 90 minutes from what locals call “North County” to “South County,” exudes elegance with its tidy farms, historically preserved homes and main streets offering everything from farm-to-table fare to boutiques that feel like they could be in Brooklyn. No matter the town you pick to use as your base of exploration, you’ll find plenty to do. We chose Pittsfield as our starting point for a Berkshires immersion and an overnight at Hotel on North, the town’s only boutique hotel, does not disappoint. Every nook and cranny of the hotel’s two historic 19th-Century buildings have been restored and it was cool to discover the character of this 45-room hotel, once a thriving menswear and sporting goods store. While you’re there to browse through Dory & Ginger, which stocks gifts and jewelry from local artists.
While you’re in Pittsfield, be sure to pop by the Hancock Shaker Village, which sports 750 acres of outdoor activities. At the Discover Barn, a 1910 barn/hands-on center, kids can take turns spinning wool, constructing a Shaker chair or weaving on a kids’-sized loom.
Then, once you’ve gotten your fill of life on the farm, continue your Berkshires adventures by taking a scenic drive down the always interesting Route 7 to Great Barrington and explore this town, considered one of the best in the Berkshires for shopping, award-winning dining and strolling the historic streets. Before you leave, head on over to SoCo Creamery, an all-natural ice cream shop that’s used locally sourced ingredients since 1989.
Kitschy fun in the Catskills
To say there has been a Catskills revival in recent years is an understatement. Once neglected main streets have gotten a major reboot in this mountainous region two-plus hours to the north of us and the days of a dingy overnight stay in a side-of-the-road motel has given way to accommodations in very stylish boutique hotels. Consider anchoring your Catskills stay at the Emerson Resort & Spa, a luxury property in Mount Tremper, New York, which is located right in the midst of Catskill Park. Best of all, there’s a kid-friendly atmosphere here that your little ones will very much appreciate. For example, the resort’s game room features, ping pong, Nintendo Wii and plenty of board games and, most recently, the Emerson introduced a Kids Movement class for ages 4-8, which encourages youngsters to explore and express creative movement in a safe playful environment. Your kids will also love checking out the resort’s World’s Largest Kaleidoscope, which is housed in a 60-foot high barn silo.
While you’re at the Emerson, make sure to stop in for breakfast or lunch at the Phoenicia Diner, a local fave, located right down the road. Another must-stop that’s just a 20-minute drive: Woodstock, New York, a family-favorite for its easy-to-access to the Shawangunk Mountains, which offer 78 miles of trails for hiking and biking (in varying levels of difficulty). Be sure to fuel up at Bread Alone, known for its certified organic breads and twice baked almond croissants, before you hit the trails.
If you’re in search of another adventure, exit in Kingston, an old Dutch town that was New York’s first capital. While you’re in town, walk the downtown stockade historic district of shops and restaurants, which contains 21 of these gorgeous houses, and be sure to fuel up at Duo Bistro, a lively eatery with a tasty assortment of burgers, including the Moo-Cluck-Oink, before heading on to Roxbury, a tiny town that’s home to the Roxbury Motel, which calls itself a “boutique motel resort.” This one-of-a-kind truly fabulous hotel features individually designed rooms that are unforgettable, including The Shagadelic, to hearken back to Austin Powers, and George’s Spacepad, which has a decorative style that will prompt you to feel like you’re sleeping on another planet. There are board games and DVDs galore for families to enjoy together, should it be a rainy day, the spa and relaxation room overlooking a roaring brook is pure heaven and the hot tub, steam room and sauna are another must for exhausted parents to rejuvenate. Within a five-minute walk from the motel: The tiny town of Roxbury, which boasts the cool and quirky Roxbury General, an inventive shop loaded with giftable treats, locally sourced artisanal items and kids toys, and Cassie’s (soon to be Chappie’s) Café, which serves top-notch breakfast, lunch and dinner and a menu offering something yummy for even the pickiest of eaters.
Kid-friendly everything in the Poconos
As you get closer to the glorious Poconos, which take up 2,400 square miles in northeast Pennsylvania, we promise your kids are going to start getting excited. That’s because they won’t be able to miss all the roadside signs that begin to appear promising endless fun and adventure as you drive down the region’s gorgeous rolling mountain roads. Located just an hour and 45 minutes from New York City, the Poconos were once the place to go for honeymooners but have transformed into a year-round family-friendly destination offering 261 miles of hiking and biking trails, whitewater rafting, boating, swimming, zip lines, fishing, and year-round cultural events.
We decamped at Woodloch Resort recently to experience a fully immersive family-friendly getaway and the family-owned property did not disappoint. Not only are there kid-friendly activities on the half-hour—and you really feel like everyone wants you to have fun—the staff is super friendly and willing to help direct you to the activity of your choice. It doesn’t matter if the weather isn’t ideal, either, as there’s a massive indoor water space on property that features splash pads, tubes, a Jacuzzi, sauna, and pool bar for mom and dad.
And, if you have a little extra time, consider driving down the road to Hawley, Pennsylvania, the home of the renovated Hawley Silk Mill, a massive mill built in 1880 that operated as a Silk Mill until 1956, which has been recreated as a space that now features shops and galleries. Take a few minutes and stop for coffee at the Cocoon Coffee House & Bakery, housed in a cozy adjacent building that once sheltered the cocoons that supplied the silk.
Finally, while you’re in the area, be sure to make time to pop on over to Kalahari Resorts, America’s largest indoor water park, located in nearby Pocono Manor. The park features a retractable roof and 220,000-square-feet of indoor rides, slides, a surf simulator and splash pools. A full day at the resort (day passes are available) will yield endless moments of fun on twisting waterslides, a ride along a lazy river and poolside cabanas available for rent.