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

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.

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.

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.

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.

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.)