Windsor Locks, Connecticut, is only about two hours west of Boston, but why not use the drive as a chance to do a little exploring? And, sure, you could see some of the more mainstream places in this part of New England, like Martha’s Vineyard, Plymouth Rock, or the Franklin Park Zoo, but sometimes, the road less traveled is just too much fun to pass up—especially if you’ve already seen the headlining attractions in Massachusetts, Rhode Island, and Connecticut. This eccentric road trip from Massachusetts to Connecticut will take you through some of the most niche, unconventional, and underrated spots in New England… Keep reading to see what you don’t want to miss when driving from Boston to Windsor Locks!
Brookline is only about 30 minutes southwest of Downtown Boston, but it’s still worth a stop on your way to Windsor Locks. Some of the most popular attractions in Brookline include the John Fitzgerald Kennedy National Historic Site, Emerson Garden, and the Frederick Law Olmsted National Historic Site. But, another great place to go in Brookline is Larz Anderson Park a beautiful, sprawling green space on the outskirts of town where you’ll also find the Larz Anderson Auto Museum. Boasting the oldest car collection the country, the Larz Anderson Auto Museum is a can’t-miss stop for automobile enthusiasts, and even if you don’t consider yourself much of a gearhead, it’s still a pretty cool place to explore.
Open Tuesday through Sunday from 10 am to 4 pm, the museum hosts temporary exhibits in addition to its permanent collection, which showcases the vintage cars purchased and preserved by the museum’s namesake, Larz Anderson and his wife, Isabel. The collection includes vehicles that date all the way back to 1899, and in the 60 years since the museum’s grand opening, the Larz Anderson Auto Museum has blossomed into a cherished educational institution that provides a window to the past through the lens of car technology and its evolution. General admission is $10 for adults and $5 for seniors, military personnel, students, and children ages 6 to 12.
About an hour southwest of Boston, Sharon, Massachusetts, is a quaint New England town that makes for a charming place to take a break from the car and stretch your legs. A few of Sharon’s local restaurants include Coriander Bistro, Todd’s Deli, Mick Morgan’s, and Alice’s Mandarin Taste. And while you’re in this part of the state, make sure that you check out the Moose Hill Wildlife Sanctuary, just west of Sharon’s town center, where you’ll find hiking trails, protected forests, and a nature center.
Encompassing nearly 2,000 acres, the Moose Hill Wildlife Sanctuary is the perfect place to get in touch with New England’s natural side. (The most common animals found in Massachusetts include beavers, rabbits, deer, woodchucks, foxes, coyotes, moose, bobcats, bears, ducks, and turkeys!) The sanctuary features 20 miles of trails and a weekend farm stand during the summer months, and while the landscape is gorgeous year-round, one of the best times to go is during the fall when the leaves are changing colors.
Around an hour southwest of Boston, Providence is both Rhode Island’s biggest city and the state’s capital, which means that there’s plenty to do and see. Some of Providence’s most-visited attractions include the Roger Williams Park Zoo, the Rhode Island School of Design Museum of Art, Kennedy Plaza, Historic Federal Hill, Waterplace Park, and, of course, the Rhode Island State House. Another cool spot to go in the city is the Providence Athenæum, an educational institution that dates all the way back to 1836.
An extensive library with many prestigious volumes stocked within its walls, the Athenæum has had many famous names pass through its doors, including writer Charlotte Perkins Gilman, 37th Secretary of State John Hay, horror writer H. P. Lovecraft, and, perhaps most notably, Edgar Allan Poe. Based inside a Greek Revivalist building, the Athenæum is comprised of the main library, a children’s library, a reading room, and a rare books room, which is only accessible by appointment. Plus, in addition to books, you’ll also find paintings, sculptures, and other pieces of art at the Athenæum.
Just south of Providence, Warwick is Rhode Island’s second-largest city, and, having been founded in 1642, it’s a town where history can be found around every corner. Among the best places to immerse yourself in Warwick’s rich heritage are Clouds Hill Victorian House Museum, Warwick Neck Lighthouse, Apponaug Village, and Gaspee Point. But, don’t worry—Warwick isn’t only a destination that history buffs will love. Other popular attractions include Rocky Point State Park, Warwick Center for the Arts, and Buttonwoods Beach. And, if you’re in the mood to do some learning that’s not history, check out the Biomes Marine Biology Center, a hands-on learning facility that specializes in marine biology.
Open daily from 12 pm to 5 pm, the Biomes Center has a collection of fish, crustaceans, and amphibians that you can see up-close—and, some of which, you can even touch. While modest in size, the center features interactive experiences and a knowledgeable, friendly staff that will be happy to show you around and introduce you to all of the center’s inhabitants. Admission is $11 for adults and $9 for seniors and children ages 3 to 12.
Middletown, Connecticut, is around 30 minutes south of Windsor Locks, and it’s a lovely riverside city that’s best known for housing the private liberal arts college Wesleyan University. The city’s highlights include the Kidcity Children’s Museum, Wadsworth Falls State Park, the Samuel Wadsworth Russell House, and Harbor Park. But, if you’re the kind of starry-eyed person who’s always got your head in the clouds, then we’ve got the perfect place for you: the Van Vleck Observatory at Wesleyan University.
Built in 1914, Van Vleck Observatory is more than just an enriching attraction—it’s a long-revered monument to education. From historical artifacts to modern technology, the facility is equipped with everything that any aspiring astronomer (or curious traveler) needs to entertain themselves for a few hours. The observatory regularly hosts public events, when visitors can look at the night sky through the research-grade telescopes. (No events scheduled while you’re in town? You can schedule a tour of the facility—at night or during the day!)
About 50 minutes southwest of Windsor Locks, Thomaston, Connecticut, might seem a little out of the way, but this delightful town more than makes up for the slight detour! A few of the leading attractions in and around are Cricket Hill Garden, the Thomaston Opera House, Spruce Hill Farm, and Black Rock State Park. But, if you’re looking for an unforgettable New England experience, then you don’t want to bypass the Railroad Museum of New England, a not-for-profit organization with a mission to preserve and share the region’s roots in the railway industry.
Though it might have the word “museum” in its name, the Railroad Museum of New England isn’t you’re traditional museum—rather, the organization gives visitors the chance to board an actual train and take an excursion ride through the area in order to learn more about the Naugatuck Railroad and its history. With seasonal events, like the Easter Bunny Express, the Northern Lights Limited, the Santa Express, and a pumpkin patch ride, as well as scenic and historic tours, the Railroad Museum of New England is a family-friendly attraction that will help you to get to know New England, its past, and its present like never before.
Close to 20 minutes south of Windsor Locks, Hartford is Connecticut’s capital city, and with a wealth of history and culture—not to mention ample green space—it makes for an ideal last stop before finally arriving at your destination. Some of Hartford’s top attractions include the Mark Twain House & Museum, the Connecticut Science Center, the Elizabeth Park Conservancy, the Harriet Beecher Stowe Center, Bushnell Park, and the Wadsworth Atheneum Museum of Art. And, because Hartford is the state capital, you don’t want to miss a trip to the Connecticut State Capitol while you’re in town. But, Hartford doesn’t just have one capitol building—it actually has two, the modern-day one and the former one, also known as the Old Connecticut State House, which was originally completed in 1796.
In addition to being a great place to learn about Hartford, Connecticut’s political history, and American democracy in general, the Old Connecticut State House houses a wonderfully weird assortment of rare items and obscure keepsakes—this is known as the Museum of Natural and Other Curiosities. Some of the State House’s most prized possessions include Mark Twain’s bicycle and a two-headed calf, and the building itself is rumored to be haunted. (The museum is actually the city’s way of paying homage to long-ago Hartford resident Joseph Steward, who displayed his own similar collection of curiosities in the 1800s.)
Located in the northern portion of the central part of the state, Windsor Locks is seated along the edge of the Connecticut River and is roughly equidistant from the state capital, Hartford, and Springfield, Massachusetts. Among the most popular places to go in and around Windsor Locks are the New England Air Museum, the Connecticut Trolley Museum, and the Vintage Radio & Communications Museum of Connecticut. West of the town, you’ll find Penwood State Park and Talcott Mountain State Park, both of which are ideal places to admire New England’s colorful scenery and natural beauty. While you’re sure to fall in love with Windsor Locks’s small-town charm and welcoming aura, don’t make the mistake of rushing to get there from Boston and missing out on all of the cool, offbeat places on the way! After all, you know what they say about the road less travel—it can make all the difference.