6 Excursions That Let You Squeeze the Last Bit Out of Summer…or Kick-Start Fall

While fall technically doesn’t start until September 23, it definitely feels like summer is over. But even though it’s time to swap our swimsuits for sweaters, there are plenty of weekend jaunts that let you keep up the season’s carefree spirit for a while longer. From festivals and fairs to sunset sails and adult summer camp, here are some great ways to really squeeze out every last ounce of summer—or dive headfirst into autumn. You decide.

The 7 Prettiest Places to See Fall Foliage Near New York City

early fall getaways near nyc club getaway
Courtesy of Club Getaway

1. Club Getaway (kent, Ct)

Just an hour and a half from the city in the Berkshires, this adult summer camp extends into the fall with its season finale from October 4 to 6. Earlier in the year, the all-inclusive weekend might include water skiing and volleyball, but for this edition expect touch football games, hayrides, pumpkin carving and even a haunted house and themed costume party—against a backdrop of top-notch fall foliage, we might add. Arrive by car or take advantage of the specially arranged bus service directly from Manhattan.

early fall getaways near nyc harbes family farm
Courtesy of Harbes Family Farm

2. Harbes Family Farm (mattituck, Ny)

Now that Hamptons traffic is a thing of the (not-so-distant) past, zip out to the North Fork for outdoor activities at breweries (like Jamesport Farm Brewery in Riverhead) and wineries (like Kontokosta Winery in Greenport) or really get into the spirit of the season at Harbes Family Farm in picturesque Mattituck, with its Apple Festival (Sept 18 and 19) and Pumpkin Festival (September 28 and 29). Or just stop by any weekend for a glass of wine from the farm’s on-site vineyard.

3. Skywalk Arts Festival (hudson, Ny)

Explore the best of the Hudson River Valley at the Skywalk Arts Festival on September 22. The fest centers around the Hudson River Skywalk, a brand-new pedestrian path over the Rip Van Winkle Bridge spanning Hudson and Catskill that offers exhilarating vistas of the river and beyond. The region is famously the birthplace of American landsape painting, so celebrate with artist exhibitions, musical performances, painters “en plein air” on the bridge and beginner art lessons. If you’re a fan of art or architecture, be sure to visit the neighboring historical homes of 19th-century painters Frederick Church Olmstead and Thomas Cole.

early fall getaways near nyc canoeing
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4. Lumberton Fall Festival & Paddle (lumberton, Nj )

Boating season may be drawing to a close, but you can still get out on the water at the Lumberton Fall Festival & Paddle on September 21. Cruise down the Rancocas Creek in a $20 rented canoe (or bring your own), then when you complete the one-hour trip, hop into one of the all-day shuttles back to the Village Green, where you’ll find live music and family-friendly activities like pumpkin painting.

early fall getaways near nyc wellfleet oyster festival
William Pomeroy

5. Wellfleet Oysterfest (wellfleet, Ma)

By October, it will be too chilly to take a dip in the ocean, but with all the shark sightings off Cape Cod this summer, maybe that’s a good thing. You can still (quite literally) get a taste of the sea at Wellfleet’s annual OysterFest (October 19 and 20), which celebrates the outer Cape’s famed shellfish with food, art, music, games and plenty of the mouthwatering mollusks. Bonus: The off-season is actually a great time to explore Cape Cod like a local.

early fall getaways near nyc classic harbor line cruises
Courtesy of Classic Harbor Line

6. Classic Harbor Line Cruises (new York, Ny)

Looking for an end-of-summer activity a little closer to home? Classic Harbor Line offers sailing excursions around New York Harbor on a selection of five classic yachts—two sailboats and three motorized—reminiscent of the boats that circled the city during the 19th and 20th centuries. Enjoy a sunset cruise aboard the Schooner America 2.0, modeled after the winner of the first America’s Cup in 1851, or channel your inner Zelda and F. Scott Fitzgerald aboard the 1920s-style mahogany-trimmed yachts Manhattan and Manhattan II. (With cocktails, of course.)