As summer 2024 winds down, you might find yourself scrambling for a last-minute Labor Day weekend getaway. But don’t fret—there’s still time to squeeze in one final adventure before the season officially says goodbye. Whether you’re craving the great outdoors, a sun-soaked beach, or a cultural escape, here are four perfect destinations just a short trip from New York City.
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1. Litchfield, Connecticut: A Timeless Escape
Litchfield County has long been the countryside retreat of choice for New York’s elite. Imagine rolling hills, charming stone barns, and farm stands brimming with fresh produce. If you’re planning to visit, consider staying at the Mayflower Inn, a luxurious spot set on 58 acres that offers everything from tennis to archery—and a spa that’s simply divine. New to the area? Check out The Abner, a 20-room boutique hotel with a farm-to-table restaurant, opening just in time for Labor Day. Review the “Visit Litchfield Website”, click here.
2. Hudson Valley, New York: Where Nature Meets Culture
Stretching from the tip of New York City all the way to Albany, Hudson Valley is vast and beautiful. But with so much ground to cover, where should you go? Some of our favorite towns include Kingston, Tivoli, Rhinebeck, and Hudson. Each one boasts charming farm-to-table eateries, vibrant art scenes, and unique mom-and-pop shops. If you’re after luxury, check out hotels like Inness, Troutbeck, or Wildflower Farms for a stay that combines sprawling grounds, soothing spas, and exceptional service. For a more urban vibe, consider Hotel Kinsley or The Maker, both conveniently located on bustling Main Streets. Here are some great ideas when visiting Hudson Valley, click here.
3. The Berkshires, Massachusetts: Literary and Leisurely
Once the go-to getaway for Bostonians, The Berkshires have now become a favorite for New Yorkers too, especially after Amtrak launched a service from Penn Station in 2022. This picturesque region is steeped in literary history—Edith Wharton penned The House of Mirth here, and Herman Melville wrote Moby Dick in the area. You can even visit their historic homes. The towns of Lenox and Great Barrington are particularly charming, filled with delightful restaurants, galleries, and independent shops. For accommodations, Tourists in North Adams and Life House in Lenox attract a hipper crowd, while Miraval Berkshires offers a sprawling wellness retreat perfect for those seeking total relaxation.
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4. Amagansett, New York: Hamptons Charm at Its Best
When it comes to the Hamptons, you can’t go wrong with any town, but Amagansett holds a special place in our hearts. The Main Street is a perfect mix of old-school charm and modern luxury, lined with mom-and-pop stores and high-end boutiques like The Row. For fresh, local produce, head to Amber Waves Farm Stand, and if you’d rather dine out, Il Buco Al Mare offers a laid-back yet gourmet dining experience. As for where to stay, both The Reform Club and The Roundtree provide quaint yet elegant accommodations, complete with complimentary bike cruisers to take you straight to the pristine Indian Wells Beach. Want to find out what to expect when visiting Amagansett? Click here.
So why wait? Pack your bags, hit the road, and make the most of your Labor Day weekend with one of these unforgettable getaways. Summer may be ending, but the memories you’ll create will last a lifetime.