Highlights:
Head south from Hartford on I-91 and in about 40 minutes you’ll reach New Haven, home of Yale University. Stop by for a stroll on Yale’s beautiful campus (it’s free to walk around and offers guided tours for visitors) and grab a slice of the legendary New Haven–style pizza at Frank Pepe Pizzeria Napoletana on Wooster Street. Locals just call it Pepe’s opened in 1925, it’s one of the oldest and most famous pizzerias in the country and trust us, it’s worth it for an early lunch of their coal-fired pies (the white clam pizza is a classic).
After New Haven, continue east along the Connecticut shoreline on I-95. If you have time, consider a quick pit stop in Old Saybrook or Essex charming small towns on the Connecticut River or just head straight to Mystic. In Mystic, plan to spend a few hours. You can check out the Mystic Seaport Museum, a recreated 19th-century seafaring village with historic ships and buildings, or visit the Mystic Aquarium to see beluga whales and African penguins up close. Don’t forget to snap a photo at the famous Mystic Pizza (the real pizzeria made famous by the 1988 Julia Roberts movie). Grab an ice cream downtown and enjoy the harbor views before moving on.
From Mystic, cross into Rhode Island and head toward Newport, arriving by late afternoon. Newport is famed for its opulent Gilded Age mansions you can tour The Breakers (Cornelius Vanderbilt II’s extravagant 1895 summer home) or another mansion like Marble House if time permits. A drive along Newport’s Ocean Drive offers stunning coastal scenery, and a must-do is the Cliff Walk, a scenic 3.5-mile public walking trail along the shoreline that runs behind the mansions (it’s free and open to the public year-round; even walking a portion gives spectacular ocean views). In the evening, the Newport harbor area is lovely consider dinner at a seafood restaurant on the wharf (fresh Atlantic lobster or a cup of New England clam chowder is a perfect New England treat). Finally, head back to Hartford by a more northerly route for a change of scenery. Take I-95 west to I-395 north, then CT-2 west; this roughly 2-hour drive will lead you through the quiet forests and small towns of eastern Connecticut, a relaxing end to the day.
Pro Tip: This trip can be a packed single day or a relaxed two-day adventure. If doing it in one day, get an early start and be mindful of the time you spend at each stop it’s a lot to cover. If you have two days, consider overnighting in Mystic or Newport (Newport especially has great B&Bs and historic inns). Summer traffic heading into Newport can bottleneck, especially on weekends, so try to visit on a weekday or arrive early in the day if possible. On a two-day trip, you could enjoy a sunset in Newport and a leisurely morning the next day before heading back.
Pro Tip: Newport’s Cliff Walk is free and open to everyone, but wear good walking shoes as parts of the path are uneven or rocky. In the summer, Rhode Island’s beaches (like Easton’s Beach in Newport or Misquamicut State Beach back near Mystic) are a big draw if it’s hot out, pack swim gear and towels in case you want to take a dip in the ocean. Finally, keep some small bills/coins handy: parking in Newport near the wharfs and mansions often uses meters or pay kiosks, so having quarters or small bills will make parking easier.