Ann Arbor to Montauk Road Trip: Ultimate Guide

The road from Ann Arbor, Michigan to Montauk, New York stretches over 850 miles and traverses eight states. This route follows Interstate 94 east to the New York State Thruway (I-87) before cutting south across Long Island. A little-known fact: the Long Island Expressway (I-495) ends inexplicably at County Road 111, not Montauk, requiring a final push on NY-27. This trip typically takes 13–14 hours of pure driving, but planning stops transforms it into a multi-day adventure. Many travelers ask: how to find the best stops and hidden gems between cities—the answer lies in strategic route deviations.

Fuel costs vary significantly across states. As of 2025, Ohio averages $3.00/gal, New York $3.50/gal. Toll roads include the New York State Thruway (I-87) and portions of I-95 in Connecticut. E-ZPass is accepted; cashless tolling is common. Rest areas on I-90 in New York occur every 30–50 miles. Plan for two fuel stops: near Erie, PA, and one in the Hudson Valley. Consider using apps to track diesel vs. gasoline prices.

• Ohio: average $3.00/gal, many truck stops
• Pennsylvania: average $3.20/gal, limited exits near I-86
• New York: average $3.50/gal, higher near Montauk

Road quality is generally excellent on interstates, but NY-27 east of Westhampton can be congested in summer. Best months to drive: May–June or September–October to avoid traffic.

Interstate driving is safe, but watch for deer in rural New York. Family-friendly stops include the Strong National Museum of Play in Rochester, NY, and the Mystic Aquarium in Connecticut. Pet-friendly motels: Motel 6 and La Quinta accept dogs; many rest areas have pet walks. Fatigue management: stop every 2 hours. Ideal rest zones are service plazas on the Thruway, with food and restrooms.

• Family stops: Strong Museum (Rochester), Mystic Aquarium (CT)
• Pet-friendly: Rest areas with fenced dog runs on I-87
• Safety: High accident rates on I-287 near White Plains; use caution

Hidden off-route spots: Letchworth State Park (NY) known as the Grand Canyon of the East, and the North Fork of Long Island for wine tasting. Local culture: visit farm stands on the East End of Long Island for fresh produce.

As you leave Ann Arbor, the Huron River valley gives way to farmland. Near Cleveland, Cuyahoga Valley National Park offers a quick detour—Brandywine Falls is a must-see. Further east, the Finger Lakes region near Watkins Glen provides gorges and waterfalls. UNESCO sites worth a stop: no direct UNESCO sites on route, but the Statue of Liberty (NYC) is a short detour off I-95. Local commerce thrives in towns like Hudson, NY, with antique shops on Warren Street.

• Natural attractions: Cuyahoga Valley National Park, Watkins Glen, Montauk Point State Park
• Cultural hubs: Hudson (antiques), North Fork wineries, Montauk fishing villages

Climate varies: expect humid summers in Ohio, mild coastal breezes on Long Island. Fall foliage peaks mid-October in New York. Winter driving can be treacherous in the Catskills—check forecasts.