Hartford sits in the middle of just about everything New England does well. In an hour or so you can be at a working seaport, on the country’s most famous pizza street, deep in covered-bridge country, or wandering a museum in the mountains. And since this is a cheap-eats site, we’re not sending you anywhere without telling you where to eat for a few bucks along the way. Here are five easy road trips from Hartford, each with verified cheap stops to keep you fueled.
💡 Before you go: Gas up and grab breakfast in town first — our Hartford cheap-eats list has spots where two eat for under $20. Then pick a direction.
About an hour southeast on I-95. A postcard New England seaport — the Mystic Seaport Museum’s tall ships, the Mystic Aquarium, a drawbridge over the river and a walkable downtown of shops and ice cream. And yes, the pizza place from the movie is real. Where to eat without spending Gilded-Age money:
About 45 minutes south — and the most important pizza pilgrimage in America. New Haven’s coal-fired, thin-crust “apizza” (say “ah-BEETS”) has been called the best in the country, and it started here in 1925. Add Yale’s campus, museums and the Green. Come hungry. (New Haven’s one of our 2for20 cities, too — see the full cheap-eats list.)
About an hour northwest, into Connecticut’s quiet corner. Rolling hills, covered bridges, Kent Falls tumbling 250 feet, antique shops and Main Streets that look painted — the state’s most scenic drive, and spectacular in October. Refuel in the villages:
About an hour north, into western Massachusetts. Norman Rockwell’s Stockbridge, Tanglewood’s summer concerts, Edith Wharton’s mansion and MASS MoCA’s giant galleries, all wrapped in mountain scenery. Rockwell painted the diner here — and you can eat in it:
About 90 minutes east, on the Rhode Island coast. Gilded Age mansions like The Breakers, the three-and-a-half-mile Cliff Walk between the cliffs and the sea, a historic harbor and cobblestone Thames Street. It’s a splurge town — but the Rhode Island seafood classics stay cheap:
🍂 Two-season tip: These drives are jaw-dropping during peak fall foliage (mid-October) — but so are the crowds, so go early. In winter, the Litchfield Hills and Berkshires get real snow; check road conditions, and note that seasonal seafood shacks like Sea Swirl close for the cold months.
You don’t need a big budget or a long weekend to get out of Hartford. Every one of these trips pairs a classic New England drive with a cheap bite — a movie-famous pizza, a coal-fired apizza, a diner Norman Rockwell immortalized, a bowl of chowder by the harbor. Fuel up in Hartford, point the car, and go.
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Verified cheap eats where two people eat for under $20 — in Hartford, New Haven and beyond.
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