Seeking a last-minute Labor Day getaway? With the holiday weekend just under two weeks away, the end of summer is now officially on the horizon. But, don’t worry, procrastinators—there’s still plenty of time to plan one last hurrah.
Whether you’re looking to explore the great outdoors, tan on the beach, or take in a cultural scene, here are the best places to send off the season if you’re traveling from New York City.
Litchfield, Connecticut
The Mayflower Inn in Litchfield, Connecticut.
Photo: Courtesy of Mayflower Inn
For decades, Litchfield County has been a beloved country escape for notable New Yorkers, from Oscar and Annette de la Renta to Diane von Furstenberg, who all fell for its stone barns, rolling hills, farm stands, and small-town charm. Stay at the Mayflower Inn, which sits upon 58 acres and offers everything from tennis, to croquet, to archery—and also has an excellent spa. New to town? The Abner, a 20-room boutique hotel with a farm-to-table restaurant that opens this Labor Day weekend.
Hudson Valley, New York
Kingston, New York—one of the must-visit towns in the Hudson Valley region.
OlegAlbinsky
Hudson Valley is a large, bucolic region that technically stretches from the tip of New York City to Albany New York. So within those hundreds of square miles, where do you go? Our favorite towns include Kingston, Tivoli, Rhinebeck, and Hudson itself. (All of them, with their farm-to-table restaurants, art scenes, and mom-and-pop shops, are worth the visit. But here’s a dedicated guide to the latter.) There’s also a number of luxury hotels, from boutique inns to five-star resorts that are perfect for Labor Day getaways: stay at Inness, Troutbeck, or Wildflower Farms if you want sprawling grounds with spas and top-notch service; meanwhile, Hotel Kinsley or The Maker sit right upon their respective towns’ Main Street. A full list of our favorites can be found here.
The Berkshires, Massachusetts
The Mount, Edith Wharton’s home in Lenox, Massachusetts.
Daniel Hanscom
While the Berkshires were once considered more of a Boston getaway than a New York escape, in 2022, Amtrak launched a service to the region from Penn Station. Ever since, a new wave of New Yorkers has headed out to explore the Massachusetts countryside that is steeped in literary history: Edith Wharton wrote The House of Mirth here, and Herman Melville wrote Moby Dick. (You can visit both of their homes.)
The towns of Lenox, Massachusetts and Great Barrington are of particular note, with their restaurants, galleries, and quaint independent shops. Meanwhile, hotels like Tourists in North Adams and Life House in Lenox attract a cooler crowd. But if you’re really looking to get away from it all? Head to Miraval Berkshires, a sprawling wellness retreat that’s one of Vogue’s top 100 spas in the world.
Amagansett, New York
The Reform Club in Amagansett.
Photo: Ally Martin
You can’t go wrong with any town in the Hamptons, but Amagansett exudes a special kind of East End charm: the Main Street is still lined with mom-and-pop stores (and, well, The Row) while the Amber Waves farm stand sells some of the freshest produce on Long Island. Don’t feel like cooking? Visit the acclaimed yet utterly unpretentious restaurant Il Buco Al Mare. As for your lodgings, quaint bed and breakfasts like The Reform Club to The Roundtree provide simple yet elegant service. Each hotel has complimentary bike cruisers, which you can ride straight to the pristine Indian Wells Beach.
