The Best Things to Do on a Road Trip from Brookline, MA to New Haven, CT

Brookline, Massachusetts and New Haven, Connecticut are two popular destinations located only two hours apart. If you're planning a road trip between these two cities, there are plenty of sights and attractions to enjoy along the way. From stunning coastal vistas to charming small towns, this road trip itinerary has everything you need for a memorable journey.

Located halfway between Brookline and New Haven, Union, CT is a small town that's worth stopping at. It's home to a beautifully preserved historic district, complete with 18th and 19th century homes and buildings. Unionville also boasts shops and restaurants perfect for a mid-trip break.

The Top Five Things to Do

1. Explore the Mystic Seaport Museum

Located just a short detour off the main route, the Mystic Seaport Museum in Mystic, Connecticut is one of the area's most popular attractions. The museum is an outdoor maritime museum that features tall ships, a working shipyard, and exhibits about American maritime history. Visitors can climb aboard the historic ships, watch live demonstrations of traditional shipbuilding techniques, and even try their hand at rowing a small boat.

Interesting fact: The museum's most famous vessel is the Charles W. Morgan, the last wooden whaling ship in the world.

2. Stroll the Boardwalk in Old Saybrook

Just a few miles off the main route, Old Saybrook, Connecticut is a picturesque small town with plenty to offer. One of the town's most iconic features is its boardwalk, which stretches along the Connecticut River. Visitors can stroll along the boardwalk, take in views of the river, and enjoy the town's charming New England architecture.

Interesting fact: Old Saybrook was the inspiration for the town of Kingsbridge in the novel "A Gentleman in Moscow" by Amor Towles.

3. Tour Yale University

No trip to New Haven would be complete without a visit to Yale University. One of the world's most prestigious Ivy League institutions, Yale University offers public tours that take visitors through its stunning Gothic architecture and beautiful courtyards. Visitors can also view the art collection at the Yale University Art Gallery, which includes works by Picasso, van Gogh, and other masters.

Interesting fact: Yale University was founded in 1701, making it one of the oldest universities in the United States.

4. See the Gillette Castle State Park

Located in East Haddam, Connecticut, the Gillette Castle State Park is a must-see for anyone who loves history or architecture. The park's main attraction is the Gillette Castle, a stunning mansion built in the early 20th century by the famous actor William Gillette. The castle features unique architectural elements, such as secret passages and hidden rooms, and offers incredible views of the Connecticut River Valley.

Interesting fact: The Gillette Castle was built to resemble a medieval fortress, complete with turrets and battlements.

5. Relax at Hammonasset Beach State Park

At the southern end of the trip, Hammonasset Beach State Park is a great place to unwind and enjoy some time in the sun. The park boasts a two-mile-long sandy beach, as well as hiking trails, nature exhibits, and picnic areas. Visitors can also go fishing or crabbing in the park's tidal river.

Interesting fact: Hammonasset Beach State Park is the largest shoreline park in Connecticut, spanning over 900 acres.

Conclusion

This road trip from Brookline, Massachusetts to New Haven, Connecticut offers a variety of attractions for all types of travelers. From maritime history to stunning coastline, and from small town charm to world-renowned university campuses, there's no shortage of things to see and do along the way. The route takes around two hours without stops, but with so many interesting sights along the way, why rush? Take your time and enjoy the journey.