The Montauk Yacht Club Guide: Things to Do on Long Island This Fall

Where to Move: Best Montauk Hikes & Coastal Trails in Fall

Autumn on Long Island is best experienced on the trails. At the island’s easternmost tip, Montauk Point State Park offers dramatic cliffs, ocean panoramas, and a lighthouse climb that rewards every step.

Nearby parks like Camp Hero, Hither Hills, Shadmoor, and Amsterdam Beach feature a mix of wooded trails, windswept dunes, and quiet beach paths ideal for crisp morning walks or post-lunch meanders.

These untamed trails invite you to wander where every step feels like a reset, surrounded by ocean air and fall colors.

Where to Go Coastal: Fall Water Activities & TENNIS in Montauk

The Atlantic doesn’t close for the season, and neither does the sense of play. Fall is still prime time for chartered sails and sunset cruises that let you see the coastline in a new way—unhurried, open, and golden in the afternoon light.

Looking to mix a little movement into your getaway? The tennis courts at Montauk Yacht Club are open for complimentary play for hotel guests—the perfect way to stay active by the water.

Where to Connect: Long Island History & Culture

Long Island’s culture runs deeper than its shoreline. Climb to the top of the Montauk Point Lighthouse, commissioned in 1792, for sweeping ocean views and a glimpse into maritime history. Then trade the coast for open fields at Deep Hollow Ranch, the oldest working ranch in the country and a perfect spot for a scenic horseback ride.

If you’re craving something more curated, explore Sag Harbor’s art galleries, bookstores, and historic charm, or stroll East Hampton Village for high-end boutiques and tucked-away cafés.

Where to Dine: Best Montauk Restaurants for Fall Dining

Laid-Back & Local

On Ditch Plains Beach, Ditch Witch Food Truck serves up gourmet wraps, smoothies, and surfer culture in equal measure. And throughout town centers like Montauk’s Plaza, you’ll find unassuming seafood spots serving fresh catch without the fuss.

Elevated & Refined

If you’re in the mood to settle in, Long Island’s dining scene doesn’t disappoint. Try Ocean Club at Montauk Yacht Club for refined dockside dishes, or Maverick’s Montauk for modern takes on seafood and pasta.

For a rustic yet elevated meal, Harvest on Fort Pond pairs Italian classics with a side of sweeping water views.

Want more local color? Drop into Joni’s Montauk, The Bird, Salivar’s Clam & Chowder House, or The Montauket—casual favorites with plenty of soul.

Where to Sip: Montauk Wineries & Vineyards in the Fall

Long Island’s East End is home to some of the region’s most beautiful vineyards, perfect for a fall outing. Head to Wölffer Estate Vineyard in Sagaponack for crisp rosé, seasonal tastings, and sweeping vineyard views. Or stop by Duck Walk Vineyards, a South Fork staple known for its wide selection and relaxed atmosphere.

Prefer a longer detour? Spend an afternoon on Shelter Island (a short ferry ride away) for bike rides, quiet beaches, and a slower pace that feels like a true escape.