Day Trips from Quogue: Montauk, Shelter Island, and Wine Country

One of Quogue's greatest assets is its position at the center of the East End universe. Within an hour, you can be standing at the edge of a 130-year-old lighthouse, kayaking through a wildlife sanctuary, sipping rosé in a sun-drenched vineyard, or wandering galleries in a historic whaling village. Here's where to go.

Montauk Point Lighthouse (45 minutes east)

The eastern tip of Long Island draws visitors for good reason. The Montauk Point Lighthouse — lit since 1797, the oldest in New York State — stands sentinel at the edge of the continent. Climb the 137 spiral steps to the lantern room for a panoramic view over the Atlantic, Block Island Sound, and Gardiner's Bay. Plan to arrive early on summer weekends to beat crowds and parking. After the lighthouse, explore Montauk village for lunch at one of the waterfront seafood shacks, or hike the trails at Montauk Point State Park. The drive east on Route 27 through Amagansett and East Hampton is half the pleasure.

Shelter Island via North Ferry (30 minutes)

Ship out from North Haven aboard the North Ferry — a five-minute crossing that transports you to one of the most serene places in the Hamptons. Shelter Island sits between the North and South Forks, largely car-free in spirit, with over one-third of its land preserved as the Mashomack Nature Preserve. Hike the preserve's 12 miles of trails through tidal creeks, oak forests, and salt marshes. Rent kayaks at the marina and paddle Coecles Harbor. Stay for dinner at the Shelter Island House or grab clams at a picnic table overlooking the sunset. The island is blissfully without chain restaurants or big-box stores — every meal comes from a local family.

North Fork Wine Country (30 minutes via Cross Sound)

New York's Napa sits just across the sound. The North Fork's AVA — American Viticultural Area — is home to over 50 wineries along Sound Avenue and Route 25, most with beautiful tasting rooms and pastoral settings. Standouts include Bedell Cellars for their elegant reds, Macari Vineyards for organic wines and stunning views, and Sparkling Pointe for dedicated méthode champenoise bubbles. The UNO bus runs wine country shuttles on weekends, perfect if you're planning to taste at multiple stops. The drive through Cutchogue and Mattituck feels worlds away from the South Fork crowds.

Riverhead for the Long Island Aquarium and Tanger Outlets (15 minutes)

The quickest day trip from Quogue. The Long Island Aquarium in downtown Riverhead is a family standout — sharks, jellyfish, penguins, and a butterfly garden. Plan two to three hours. Directly across the street, Tanger Outlets provides tax-free shopping at nearly 160 stores. Grab lunch at Preston's on the waterfront for chowder and lobster rolls before heading back. Riverhead is also home to the Eastern Long Island Hospital, making it the closest major medical center for Quogue residents.

Sag Harbor for Gallery Hopping and Waterfront Dining (20 minutes west)

Sag Harbor is the East End's most walkable village — and arguably its most authentic. Park once on Main Street and spend the afternoon gallery-hopping through the dozen or so contemporary art spaces, browsing the independent bookshop, and lingering over coffee at Bay Burger. The Sag Harbor Cinema, a restored 1930s theater, shows art-house films. For dinner, Tutto Il Giorno on the water is perennially beloved. The Sag Harbor Whaling Museum tells the village's extraordinary global history. Unlike the more tourist-heavy Hamptons towns, Sag Harbor feels genuinely lived-in.