Block Island to Montauk Drive: Hidden Gems & Route Guide

The route from Block Island, Rhode Island to Montauk, New York is a journey defined by ferries, coastal highways, and a transition from quiet island life to the vibrant surf culture of the Hamptons. Few travelers realize that the entire trip—including ferry crossings—covers just over 100 miles but can take a full day due to seasonal traffic on Long Island.

A local driving quirk: On Route 27 in Montauk, the road narrows to a two-lane oceanfront strip where cyclists and pedestrians share the asphalt with oversized SUVs. Patience here is a virtue.

Below is a snapshot of the key logistics:

Block Island boasts dramatic bluffs and the 200-foot Mohegan Bluffs, formed by glacial till. The Montauk Point Lighthouse sits atop a glacier-scoured moraine. The drive crosses the Connecticut River via the Baldwin Bridge and skirts the Pine Barrens of central Long Island.

Best stops Block Island, RI to Montauk, NY include the Block Island National Wildlife Refuge (spring migration), the South Fork Museum of Natural History (Bridgehampton), and the Montauk Point State Park. A UNESCO World Heritage Site is absent, but the entire region is part of the Last Green Valley National Heritage Corridor.

Is it worth driving Block Island, RI to Montauk, NY? Absolutely, for the contrast of bucolic pastures, salt ponds, and ocean vistas. Things to do between Block Island, RI and Montauk, NY: clam chowder tasting in Mystic, CT, wine-sipping in North Fork, and hiking at Hither Hills.

Road quality is excellent except for potholes near the Montauk Village. Safety: Long Island's Sunrise Highway (Route 27) is heavily patrolled between exits 70–80. Use rest areas like the one at Exit 71 (Suffolk County).

Family suitability: Stop at the Long Island Aquarium (Riverhead) or the Children's Museum of the East End (Bridgehampton). Pet-friendly: Montauk's beaches allow dogs off-season; ferry companies permit pets in carriers.

Fatigue management: Schedule a break at the Cedars Inn in East Marion (coffee and orchard views). Hidden off-route spots: The Carriage House in Southold for sunset wine and the Halsey House in Southampton (oldest English-style house in NY).

Start at Block Island Ferry Terminal on Water Street. The car ferry to Point Judith (toll $60+ per vehicle, reservation required) runs seasonally. Once on the mainland, follow Route 1 South to I-95 North, then I-95 South/East to Route 495 East (Long Island Expressway). Expect tolls totaling $8-12.

Fuel stops: Look for stations in Westerly, RI (exit 1 on I-95) and after crossing the Throgs Neck Bridge into Long Island. Gas prices in Montauk are the highest in NY. For economical driving, maintain 60 mph.

• Fuel up in Riverhead (Sunoco or Hess) before the Hamptons.
• EV charging: Tesla Supercharger at Riverhead and a slower Level 2 at Montauk Harbor.

As for how to find the best stops and hidden gems between cities, consider detouring to the North Fork wineries or a lighthouse visit in Greenport.