The Hamptons, known for its summertime allure, transforms in the fall into a picturesque haven of autumnal coziness. Trees’ leaves turn fiery red, pumpkin orange, and buttery yellow; vineyards become harvest celebration hubs; and evenings are best spent curled up near the water. Whether you’re looking for a relaxing break or a few days packed with activities, Canoe Place Inn in Hampton Bays stands as one of the best hotels in the Hamptons to host your fall getaway.
Canoe Place Inn: Your Base for Exploring the Hamptons
Canoe Place Inn, a recently revitalized historic gem, combines modern luxury with classic charm. This iconic property offers stylish suites, exceptional dining options, and easy access to the area’s fall highlights. Nestled in Hampton Bays, the inn’s waterfront views, lush gardens, and curated events make it the ideal setting for a weekend escape in the Hamptons. Here are some of the best things to do in the Hamptons in fall.
Stroll Through Sag Harbor
The quaint village of Sag Harbor, about a 30-minute drive from Canoe Place Inn, blends historical charm with cozy bookstores, chic boutiques, and gourmet cafés. The Sag Harbor Whaling & Historical Museum offers a deep dive into the rich maritime heritage of the area and is located in a Greek Revival mansion built in 1845. After a meal, take a walk along the marina.
Pumpkin Picking at Hank’s Pumpkintown
Hank’s Pumpkintown, in Water Mill, is a 15-minute drive from Canoe Place and a beloved fall destination for all ages. Set on a sprawling farm, Hank’s boasts a vast pumpkin patch, apple picking in their picturesque orchard, corn mazes, hayrides, and famous apple cider donuts.
Wine Tasting at Wölffer Estate Vineyard
Just 20 minutes from Canoe Place Inn,Wölffer Estate Vineyard in Sagaponack is home to one of the best wineries—and wine-tasting experiences—on Long Island. Sure, their rosé is a celebrated drink of the summer, but the heartier reds on offer are just as good, and are the ideal complement to taking in the fall-colored vines.
The Hamptons International Film Festival
The Hamptons International Film Festival (HIFF), which takes place in early October, attracts filmmakers, actors, and cinephiles from around the world. Screenings, panel discussions and parties take place across various venues in East Hampton, Southampton, and Sag Harbor, with the Guild Hall in East Hampton and Sag Harbor Cinema as two hubs. Whether you’re a die-hard film buff looking to catch the latest documentary feature or a Page Six–reading celebrity-hunter, this is a can’t-miss event in the fall in the Hamptons.
Explore The Parrish Art Museum
The stunning Parrish Art Museum in Water Mill features striking architecture and an enviable collection of modern and contemporary works. Furthermore, the museum’s gorgeous setting, surrounded by meadows and walking trails, invites peaceful contemplation—or just a chance to stretch your legs—with the changing leaves as a beautiful backdrop.
Fall Festivals and Fairs
SouthamptonFest, hosted in early October each year, features two days of live performances, local food vendors, and fun, family-friendly activities like a children’s scavenger hunt. A beloved part of fall in the Hamptons, this festival showcases some of the best in Southampton’s traditions and local creativity.
Hiking in Shadmoor State Park
Cooler temperatures offer a great opportunity to take some hikes and explore the Hamptons’ natural beauty. Shadmoor State Park in Montauk, with its scenic bluffs, ocean views, and tranquil trails, is a peaceful environment of 99 acres, including 2,400 feet of Atlantic Ocean shoreline.
So pack your sweaters and walking shoes and escape to the Hamptons this autumn for a weekend of wine tasting, pumpkin picking, festival-going, and seaside hiking. The best of the Hamptons in fall is best enjoyed with Canoe Place Inn as your luxurious and cozy home base.
