Hartford to Boston Road Trip: Freedom Trail & City Sights

Route: Hartford ➔ Boston, MA (via I-84 E to I-90 E, ~100 miles) with an optional side stop in Worcester, MA or in Concord/Lexington for Revolutionary War history ➔ return to Hartford (either back the same way, or as a loop via I-95 S through Providence to I-91 N, ~120 miles).

Highlights:

Craving a dose of big-city excitement or a walk through the cradle of American history? Boston is only about a 2-hour drive from Hartford (roughly 100 miles). Get an early start to maximize your day in the city leaving Hartford by 7 AM can have you in Boston by around 9 AM. Once in Boston, it’s best to park your car and explore on foot. A convenient spot is the garage beneath Boston Common (entry via Charles Street), which puts you right at the start of the Freedom Trail. The Freedom Trail is a 2.5-mile red-brick marked path that connects 16 historic sites around the city. You can stroll at your own pace, starting at Boston Common and following the trail to see landmarks like the Massachusetts State House, the Old South Meeting House, Paul Revere’s House, the Old North Church, and up to the Bunker Hill Monument in Charlestown. (If you’re up for it, climbing the Bunker Hill Monument’s 294 steps rewards you with a great view of the skyline and harbor.) Along the way, you’ll pass through Quincy Market and Faneuil Hall a perfect area to stop for lunch. Grab a bowl of New England clam chowder or a famous Boston cream pie at Quincy Market’s food hall, and enjoy some people-watching amid the historic marketplace atmosphere.

Aside from the Freedom Trail sites, Boston offers plenty of other attractions depending on your interests. Families or animal lovers might head to the New England Aquarium on the waterfront, where you can see penguins, sea turtles, and a giant ocean tank, or even catch a short harbor cruise from Long Wharf for views of the city from the water. History buffs could hop across the Charles River into Cambridge to see Harvard University’s campus (stroll through Harvard Yard and feel the academic atmosphere) or visit MIT’s campus for a techie vibe. Sports fans might make a pilgrimage to Fenway Park even if it’s not baseball season, guided tours of the ballpark are available year-round and offer a chance to sit atop the Green Monster. As late afternoon sets in, consider swinging by Boston’s North End (the city’s Little Italy). You can grab some pastries for the road the cannoli from Mike’s Pastry or Modern Pastry are famous and well worth the line. If you’d rather have dinner before leaving, the North End is filled with charming Italian restaurants on Hanover Street where you can indulge in fresh pasta or pizza.

For the drive back to Hartford, you have a couple of options. The fastest route is typically to retrace your steps via the Mass Pike (I-90 West) to I-84, but timing is everything Boston traffic in late afternoon/early evening can be heavy. If you’re not in a rush and want a more scenic return, you could drive south from Boston and take I-95 West along the coast through Rhode Island and Connecticut. This shoreline route adds maybe 30–45 minutes, but you might catch a nice sunset over the water as you drive through coastal towns. Alternatively, some travelers choose to leave Boston earlier (around 3–4 PM) to beat the rush, and stop in a smaller city for dinner. Worcester, MA, which sits along the I-90/I-290 route, has undergone a revival in recent years with great restaurants and craft breweries it makes for a convenient dinner stop to break up the drive home. No matter which way you go, the drive back to Hartford will be about 2 to 2.5 hours.

Pro Tip: Driving in downtown Boston is very different from driving in Hartford Boston’s streets are notoriously tricky, with a confusing tangle of one-ways and old colonial-era roads (there’s a running joke that many Boston roads were originally cow paths, which is why they wind every which way). If you’re not comfortable driving in city traffic, a good strategy is to park once (as at Boston Common) and use Boston’s excellent public transit (the “T”) or simply walk between major sites; Boston is quite compact in its historic center. Many Freedom Trail sites and downtown attractions are within walking distance of each other, so you won’t miss the car.

Pro Tip: Time your return to avoid the worst of traffic. On weekdays, outbound traffic from Boston on I-90 and I-84 is heaviest from about 4:30 PM to 6:30 PM. If you can delay your departure until after 6:30–7 PM, you’ll have a smoother drive home. (That could mean enjoying an early dinner in the city or doing another activity and leaving later.) Alternatively, leaving before 3 PM is another way to skip the gridlock hence the idea of an afternoon stop in Worcester or even in Providence if you took the coastal route. Keep in mind that the Mass Pike (I-90) is a toll road (your rental car’s transponder or plate pay system will take care of it). If you prefer to avoid tolls altogether, you can take a toll-free route: for example, from Boston you could go I-93 north to I-495 south, then connect to I-290 west through Worcester to I-84 no tolls on that route, but it’s a bit longer and involves more turns. Lastly, with a car you have the flexibility to do things like catch a Red Sox game at Fenway or a concert in Boston if the timing works out then drive home under the stars. It makes for a long day, but it’s completely doable and absolutely worth it for a taste of Boston, one of America’s great historic cities, all in one trip.