Famed for its summer glamour, the Hamptons takes on an entirely different beauty in autumn. Fiery red, pumpkin orange, and golden yellow leaves paint the landscape; vineyards buzz with harvest festivities; and crisp evenings invite cozy moments by the water. Whether you’re seeking a peaceful escape or an activity-filled getaway, Canoe Place Inn in Hampton Bays is one of the best hotels in the Hamptons to anchor your fall retreat.
Canoe Place Inn: A Historic Gem Reimagined
Recently revitalized, Canoe Place Inn blends historic character with modern luxury. Guests enjoy stylish suites, exceptional dining, lush gardens, and sweeping waterfront views—all within easy reach of the Hamptons’ fall highlights. As your home base, Canoe Place offers curated events and the perfect setting for a memorable autumn escape.
Here are some of the best things to do in the Hamptons this fall:
Wander Sag Harbor
About 30 minutes from Canoe Place, Sag Harbor exudes historic charm with indie bookstores, chic boutiques, and inviting cafés. The Sag Harbor Whaling & Historical Museum, housed in a Greek Revival mansion built in 1845, offers a fascinating glimpse into the area’s maritime past. Cap your visit with a stroll along the marina.
Pumpkin Picking at Hank’s Pumpkintown
Just 15 minutes away in Water Mill, Hank’s Pumpkintown is a fall favorite for families and couples alike. Apple orchards, sprawling pumpkin patches, hayrides, corn mazes, and hot cider donuts make it a quintessential autumn outing.
Wine Tasting at Wölffer Estate Vineyard
Located 20 minutes from Canoe Place in Sagaponack, Wölffer Estate Vineyard is a must-visit. While their rosé is iconic in summer, fall is the time to savor their robust reds while overlooking rows of vines glowing in autumn hues.
Curated North Fork Tour: Sights, Bites, and Flights
For a seamless way to explore beyond the South Fork, Canoe Place hosts the Curated North Fork Tour. This guided experience pairs scenic drives with tastings at celebrated wineries, craft breweries, and local eateries. It’s an insider’s look at Long Island’s wine country and artisanal food scene—perfect for couples or groups who want a memorable day trip without the planning.
The Hamptons International Film Festival
Held in early October, the Hamptons International Film Festival (HIFF) draws filmmakers, actors, and cinephiles from around the globe. Screenings, panels, and parties unfold in East Hampton, Southampton, and Sag Harbor, with Guild Hall and Sag Harbor Cinema as central venues. Whether you’re a serious film lover or just curious to spot celebrities, HIFF is a fall highlight.
Explore the Parrish Art Museum
The Parrish Art Museum in Water Mill is an architectural landmark showcasing modern and contemporary art. Surrounded by meadows and trails, it’s as much about the setting as the exhibitions—perfect for a reflective walk among the fall foliage.
Fall Festivals and Fairs
Early October brings SouthamptonFest, a lively celebration with live music, food vendors, and family-friendly fun like scavenger hunts. It’s a vibrant showcase of local creativity and community spirit.
Hike Shadmoor State Park
Cooler days are ideal for exploring the Hamptons’ natural beauty. Shadmoor State Park in Montauk offers serene trails, sweeping ocean views, and dramatic bluffs across its 99 acres, including 2,400 feet of Atlantic shoreline.
Plan Your Fall Escape
From vineyard tastings and pumpkin picking to guided tours, film festivals, and seaside hikes, fall in the Hamptons brims with cozy adventures. Pack your sweaters, bring your walking shoes, and let Canoe Place Inn be your luxurious home base for making the most of the season.
