Montauk to East Hampton: A 20-Mile Drive Worth Taking

Montauk, the easternmost point of Long Island, is a fishing village turned surf town, where the Atlantic meets Block Island Sound. Just 20 miles west, East Hampton offers a different vibe—historic windmills and designer boutiques. This drive, though brief, packs in dramatic shifts in scenery and culture.

The route runs entirely on NY 27 (Montauk Highway), a two-lane road that follows the southern shore of the South Fork. Driving time is roughly 30 minutes without traffic, but summer weekends can stretch it to an hour.

One of the first things you'll notice is the change in landscape: from Montauk's rugged glacial moraine to the flat, sandy outwash plain that characterizes much of the Hamptons. This geological transition is visible in the soil and vegetation.

The route is generally safe, but due to narrow shoulders and occasional deer crossings, caution is advised, especially after dusk. The speed limit is 55 mph in rural sections, dropping to 30 mph through hamlets.

For families, the Hither Hills State Park offers a playground and a nature center with interactive exhibits. The park also has a campground, ideal for a longer stay.

Pet-friendly: Most beaches in the area are dog-friendly off-season, but from Memorial Day to Labor Day, dogs are restricted to before 9 AM and after 6 PM on town beaches. Be sure to check specific signage.

Rest zones: There are no official rest stops on this short drive, but the parking lot at Napeague State Park offers a safe place to stretch your legs. Also, the East Hampton Town Park has benches and restrooms.

If you're feeling tired, plan to stop in Amagansett, where there are several cafés and a quiet side street to park. The Golden Pear Café is a reliable spot for coffee and a snack.

Local commerce: East Hampton's main street is lined with art galleries and upscale shops, but for a taste of local life, visit the East Hampton Historical Society's museums.

Just past Hither Hills, the road slices through Napeague State Park, a stretch of protected dunes and maritime forest. This is prime terrain for spotting deer and osprey.

For a detour off the highway, take Navy Road to the Napeague Harbor, where you can watch fishermen haul in day's catch. The nearby Lobster Roll restaurant—known as “Lunch” locally—has been a staple since 1965, serving classic fried clams.

Amagansett, the next hamlet, is a blend of farmland and beach. The Amagansett Farmers Market is a great stop for local produce and artisanal goods. Just south of the highway, the Indian Wells beach offers a more secluded swim than the crowded main beaches.

Continuing west, the road crosses the Napeague stretch—a narrow, flat isthmus with marshlands on either side. This area is a hotspot for birdwatching, especially during migration.

Hidden off-route spot: a short drive south of the highway on Further Lane leads to a network of walking trails through the Long Island Pine Barrens, offering solitude and a chance to see rare plants. Remember, these trails are not well-marked, so a map is useful.

For a broader guide on discovering such spots between cities, check out how to find the best stops and hidden gems between cities.

The first stretch out of Montauk passes the Montauk Lighthouse, a historic structure from 1796, and then climbs to the highest point on Long Island—the iconic bluffs at Hither Hills. These clay cliffs rise 150 feet above the beach, offering a dramatic overlook.

Fuel options are limited: there are only two gas stations in Montauk, and none between there and Amagansett. It's wise to start with a full tank.

• Driving time: 30 minutes (non-peak), up to 1 hour on summer weekends.
• Road quality: well-paved, narrow in parts, with sharp curves near Napeague.
• Tolls: none on NY 27.
• Traffic: heavy in July and August, especially near East Hampton village.