New York City has everything, but New Yorkers know having everything can be overwhelming. Fortunately, the Big Apple is near plenty of relaxing weekend getaway locations reachable on a tank of gas or less. Upstate, a New York vacation rental in Homer, New York, gives you access to ice skating on an old-fashioned outdoor rink. Head south to see the dinosaur in downtown Haddonfield, New Jersey, or travel north to walk through lavish gardens in Stockbridge, Massachusetts. Review these 7 top weekend getaways from New York, pack a bag, and get refreshed for Monday morning.
1. Cold Spring, New York
For pure relaxation, drive 50 miles north of Manhattan to Cold Spring, New York, in the Hudson Highlands, the state’s southeastern region. This scenic village along the Hudson River’s east bank offers great views of the United States Military Academy at West Point, across the river. Fall is a perfect visiting time, as the leaves change shades to create gumdrop-colored mountains. Stroll down Main Street, the heart of the National Historic District, with businesses, shops, and restaurants in buildings from the 1800s. Stop at Rincon Argentino for hot chocolate, espresso, or a large cone of lemon gelato, and check out Antique Alley for hard-to-find items. Cold Harbor, the waterfront park, is a great place to relax and watch the kids frolic around the Civil War-era cannon. End the evening with a dinner of comfort foods at Cold Spring Depot, a re-purposed 1893 train depot. In the morning, enjoy French toast or waffles at Silver Spoon Cafe, a relaxed eatery with kids’ menus.
2. Homer, New York
A 3-hour, 45-minute drive about 220 miles northwest of Manhattan leads to Homer, New York, just north of Cortland. The Old Homer Village Historic District’s Village Green features a fascinating mix of businesses, homes, government buildings, and houses of worship in buildings from the 1800s. A former 1830s hardware store contains apartments and shops including Bridal Barn. Snap photos of the large, ornate historic homes along South Main Street, and then stop at Sinfully Sweet Cafe for tempting desserts or a Buffalo chicken sandwich with fresh mozzarella on flatbread. For cold-weather lovers, winter is a fun time in Homer. Pack your ice skates to practice your figure-8s on the ice skating rink the fire department creates on the Green. The town celebrates Winterfest each January, with a parade, snow sculpture contest, bonfire, and fireworks.
Find the perfect New York vacation rental on Tripping.com. Tripping.com is the world's #1 vacation rental search engine with over 10 million properties!
3. Island Heights, New Jersey
Escape New York completely and visit the quiet town of Island Heights, New Jersey. Drive an hour and a half, 78 miles south from Manhattan via the New Jersey Turnpike, to this center of serenity along the Toms River. Spoiler alert – there’s no carnival atmosphere or lively boardwalk attractions. However, the Island Heights Cultural And Heritage Association operates the Cottage Museum and hosts garden tours, plant sales, and wine tasting dinners. At Playa Bowls, quench your thirst with juices and smoothies like a local. Corner Deli Cafe offers an extensive breakfast and lunch menu in a casual setting. Try the Big Scott’s Belly Buster sandwich with a side of JJ’s Disco Fries, if you dare.
4. Haddonfield, New Jersey
Drive just under two hours to Haddonfield, New Jersey, and give the kids something to talk about at school Monday morning. This small town about 90 miles southwest of Manhattan via the New Jersey Turnpike features a dinosaur in its downtown area. Discovered in Haddonfield in 1858, the Hadrosaurus foulkii skeleton was the world’s most complete set of prehistoric remains. Learn about this remarkable event at the Haddonfield’s Dinosaur Information Center. When it’s time to eat, savor homemade ravioli, meatballs, or pizza at Nocella’s Ristorante and Pizzeria. Too full for a big dessert? Enjoy three-bite cupcakes from Indulgence Cupcakery, in flavors like banana split and hazelnut cheesecake.
5. Hammonton, New Jersey
Spend a weekend in Hammonton, New Jersey, “Blueberry Capital of the World.” Located 100 miles southwest of Manhattan, this South Jersey town is about two hours away via the New Jersey Turnpike. Once there, find your thrill at Blueberry Bill Farms, a family-owned business for 50 years. Purchase blueberry plants and fresh or frozen blueberries all year round, and pick your own in season. The season typically runs from early June to mid-August. Try DiMeo Farms, another family-owned, pick-your-own-berry farm, for GMO-free, naturally grown blueberries and bushes. Call for an appointment to pick berries at DiMeo. If you can’t wait to get back to your New Jersey vacation rental to bake a pie, buy a fruit pie or two from Penza’s Pies at The Red Barn.
6. Chester, Connecticut
Approximately two and a half hours and 113-miles northeast from Manhattan leads to Chester, Connecticut. The Chester Historical Society offers free admission to the Chester Museum at The Mill, which displays the fascinating tale of a waterfall and the town’s ingenuity. Kids enjoy interacting with friendly alpacas at Chakana Sky Alpacas, where adults like shopping for warm alpaca clothing. From April through November, ride the Connecticut DOT’s Chester-Hadlyme Ferry for a scenic 8.3-mile trip across the Connecticut River. In Hadlyme, visit Gillette Castle, famous for its ornate stonework and interiors. Back in Chester, Cockaponset State Forest Pattaconk Recreation Area accommodates cross-country skiing, swimming, and fishing. Before returning to your Connecticut vacation rental or home, visit Simon’s Marketplace for a casual breakfast, brunch, or deli sandwiches on freshly baked bread.
7. Stockbridge, Massachusetts
Stockbridge, Massachusetts, is 145 miles north of Manhattan, just under three hours by car via the Taconic State Parkway. This small western Massachusetts town cradled in the Berkshires features the Norman Rockwell Museum, honoring the popular 20th-century illustrator. Stroll through the beautiful Berkshire Botanical Garden and visit Tanglewood, a world-famous music venue and summer home of the Boston Symphony Orchestra. For a unique music experience, stop by the Village Green to hear the Children’s Chime Tower, which chimes children’s songs each summer evening. Fuel up with fresh chicken quesadillas and baked goods from Sweet and Savoury before heading back to NYC.
Ready to go? Check out these amazing New York vacation rentals on Tripping.com.