road trip to Bridgeport, CT, from Boston

Let’s go to Bridgeport! My daughter and I recently embarked on a 48-hour “girls weekend” to the coastal city of Bridgeport, Connecticut. One of the great things about Bridgeport is that it’s the midpoint between the Greater Boston area and a lot of places in New York and New Jersey, so it makes for a great stop on a bigger road trip — as well as a destination in itself! From the North Shore, our on-the-road time clocked in at just over three hours. And bonus — there’s a LOT to do in Bridgeport!

Where to stay

We opted for the Homewood Suites by Hilton in Orange, CT, which offered free breakfast, a pool, accessible facilities (even the pool!), large rooms with kitchens available, and a large area in the lobby to eat that had “restaurant vibes” without the stressful “restaurant rules.” We were pleased that the pool area was especially clean and well kept.

Because Bridgeport is the most populous city in the state, there are plenty of hotel and Airbnb options — you’ll have no trouble finding whatever sort of accommodations your family prefers!

What to do

We spent almost an entire day at Connecticut’s Beardsley Zoo. We anticipated staying for a few hours and were very surprised to last until 4 p.m.! (Note that if you have a Museum of Science or Franklin Park/Stone Zoo membership, you may benefit from those reciprocity perks!) We visited one section of the zoo at a time so we could explore them all thoroughly. In addition to the 300+ animals, we loved the elephant sprinkler that was great for a hot day, the playground with all kinds of natural-looking climbing structures, the interactive park ranger kids show, and the kids science zone. The carousel and the soft serve were perfect to close out a big day! 

Beardsley Zoo in Bridgeport, Connecticut

Beardsley Park also had a lot to explore and see! This peaceful park actually surrounds the zoo, so it was very easy to find. It was designed in 1884 by the great Frederick Law Olmsted, and its 125 acres offer a (relatively) accessible playground, lots of walking trails along a beautiful river, picnic areas, and two cool stone bridges. It was the perfect place to burn off some energy and find some calm vibes before the drive back home to Boston.

The Discovery Science Center & Planetarium is a great indoor spot if your Bridgeport visit takes place during the winter or on a rainy day. This museum is full of hands-on fun to inspire curiosity in all ages of kids (and adults!).

Seaside Park is another Olmstead design worth visiting. This park features 325 acres of lush lawns, sandy beaches, and shady glades. Fayerweather Island is at the west end of the park, where walkers can cross the breakwater rocks to check out a natural wildlife preserve. And a fun fact about this park: Bridgeport’s most famous resident, 19th century circus organizer P.T. Barnum, is largely responsible for the development of the park. (There is also a Barnum Museum in Bridgeport for any circus-loving kids, but it’s temporarily closed while undergoing renovations.)

Where to eat

On our drive to Bridgeport, we made a stop in Hartford for lunch at Bear’s Smokehouse, and let me tell you, it was 100% worth the stop. Kid friendly, epically delicious, and only slightly more expensive than fast food? Yes, please!

We also enjoyed meals at Bonfire Grille in nearby Milford and Famous 50’s Diner in Bridgeport. Both were perfectly kid friendly and worth recommending!

Stops between Bridgeport and Boston

We made a stop in Westford at Kimball Farm on our way back to the North Shore to get some ice cream and play in the arcade to blow off some traffic-related steam. 

I also had a list of other potential stops along the drive in case we wanted to take our time and enjoy the sights. Some spots we talked about visiting were the Elizabeth Park Conservancy in West Hartford, CT, Old Sturbridge Village in Sturbridge, MA, Nipmuck State Forest and Bigelow Hollow State Park in Eastern CT, Crystal Caves for mini golf in Auburn, MA, and The Shops at Blackstone Valley in Millbury, MA, for lunch or shopping.


Ready to head out? Be sure to check out our tips for hotel stays with little ones before you go!

Chelsey Weaver
Chelsey is a "central Mass" girl who married her 7th-grade sweetheart. She attended both undergraduate and graduate school in Boston, then taught high school on the North Shore for seven years. After living in Winchester and Melrose for several years (and moving too many times), she and her husband finally settled in Groveland in 2015. She loves the North Shore and everything it has to offer, and she enjoys raising her daughter there. Chelsey is the community engagement coordinator for Boston Moms and is mostly a stay-at-home mom. She spends lots of time advocating for children with disabilities, arguing with insurance companies, and looking for disabled influencers, inclusive companies, and materials that celebrate neurodiversity. She avidly listens to audiobooks, hates everything about coffee, and, most importantly, loves being a mom.

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