The Ultimate Guide to the Hamptons in the Fall (2025)

As the crisp morning air of early September signals a change, the Hamptons transitions into its magnificent “secret season.” The vibrant energy of summer gives way to a golden tranquility, making autumn the perfect time for cultural exploration, outdoor pursuits, and savoring the local harvest. With ocean temperatures still comfortable and the summer crowds gone, many argue this is the best time of year to be on the East End.

At Our House Property Management, we handle every detail of your home’s care so you can take full advantage of this spectacular season. Here is your town-by-town guide to the best things to do in the Hamptons in the fall.

A Note on Off-Season Beach Access & Parking

One of the great joys of autumn is unrestricted access to our world-class beaches. After September 15th, most town beach parking lots that required a summer permit are now open to all, free of charge. This is the perfect time for long, peaceful Hamptons beach walks without the worry of parking.

Can’t-Miss Hamptons Fall Festivals 2025

• Sag Harbor American Music Festival (September 26-28): A weekend of incredible live music throughout the charming village of Sag Harbor.
• Hamptons International Film Festival (October 9-13): A highlight of the autumn season, this acclaimed festival brings world-class cinema to East Hampton and Sag Harbor.
• ARF’s Stroll to the Sea Dog Walk (Saturday, October 11): Join the Animal Rescue Fund of the Hamptons for this beloved charity event. Walk with (or without) your furry friends from East Hampton Village to the ocean, all for a great cause.
• Montauk Fall Festival (October 11-12, Columbus Day Weekend): A family-friendly tradition with live music, food, and the famous Clam Chowder Contest.

Montauk: Rugged Outdoor Activities

• On the Water: Surfing & Paddling: Fall is prime surf season in Montauk. Hurricane swells bring consistent waves to the legendary breaks at Ditch Plains Beach. For paddlers, the calmer waters of Lake Montauk are perfect for exploring.
• Hiking & Fall Foliage: The dramatic trails of Hither Hills State Park and Camp Hero State Park are spectacular. For a classic view, head to the Montauk Point Lighthouse.
• Golf & Tennis: The public course at Montauk Downs State Park offers a beautiful challenge and public tennis courts.

Amagansett: Coastal Charm & Farm Stands

• Surfing & Beach Walks: The beach break at Atlantic Avenue Beach is a popular spot for fall surfing.
• Harvest Season: A visit to a local farm stand is a quintessential fall activity in the Hamptons. Balsam Farms in Amagansett is a must-visit for fresh produce and baked goods.

East Hampton: Art, Culture, and Recreation

• Art & Culture: East Hampton is a cultural hub. Visit the iconic Guild Hall for world-class art exhibitions and performances. For a unique experience, explore the whimsical handbag designs and stunning sculpture gardens at The Leiber Collection. For a spectacular autumn experience, visit the Longhouse Reserve. The 16-acre sculpture garden is magical when framed by fall foliage.
• Paddling: The protected waters of Accabonac Harbor and Three Mile Harbor are ideal for a peaceful autumn paddle.
• Hiking: The Long Pond Greenbelt and Cedar Point County Park offer miles of scenic trails perfect for viewing changing leaves.
• Tennis: Find excellent public courts in the heart of the village at Herrick Park and at East Hampton High School (non-school hours).

Sag Harbor: Historic Streets and Seaside Paddling

• Paddling: Launch a kayak or paddleboard from Long Beach to explore the picturesque coves of Sag Harbor Bay.
• Art & Culture: Stroll Main Street and visit galleries like the Grenning Gallery and the historic Sag Harbor Whaling & Historical Museum.
• Hiking: Explore the nearby Elizabeth A. Morton National Wildlife Refuge, famous for its friendly, hand-feeding chickadees.

Sagaponack, Water Mill & Bridgehampton: The Harvest Heartland

• Picnic Lunch & Local Flavors: Stop by the iconic Sagaponack General Store for delicious sandwiches and baked goods. Without the summer crowds, it’s the perfect place to grab a picnic lunch to take to nearby Sagg Main Beach.
• Apple & Pumpkin Picking: Go apple picking in the Hamptons at The Milk Pail in Water Mill or visit Channing Daughters Vineyard in Bridgehampton. For family fun, Hank’s Pumpkintown offers pumpkin picking and hayrides.
• Family Fun: For a fantastic indoor activity, especially on a rainy day, visit the Children’s Museum of the East End in Bridgehampton. With hands-on exhibits and creative play spaces, it’s a perfect destination for kids.
• Art & Culture: Visit the renowned Parrish Art Museum in Water Mill.

Southampton: Grand Estates and Fall Activities

• Art & Culture: Southampton is rich with cultural destinations. The Southampton Arts Center always has compelling exhibitions. For local history, explore the Southampton History Museum’s multiple historic sites, including the Rogers Mansion. Delve into the area’s deep indigenous heritage at the Shinnecock Nation Cultural Center and Museum.
• Paddling & Beach Walks: The calm waters of Shinnecock Bay are perfect for paddling. A walk along Cooper’s Beach is a must.
• Biking & Fall Foliage: A scenic bike ride along Meadow Lane is a quintessential fall experience.
• Tennis: The village offers public tennis courts at Tuckahoe School and Southampton Youth Services (SYS).

Autumn is your time to enjoy the Hamptons at its most authentic. With Our House Property Management handling your home’s needs, your only task is to decide which adventure to embark on next.

Ready to experience a worry-free Hamptons fall?

Contact Our House Property Management today to discuss your property needs.