5 Road-Trip Worthy Connecticut Towns

If you're anything like us, you love a good adventure...and 2020 has made adventure look a lot different! That's why when month 6 of social distancing came and we realized our passports were just collecting dust, we hit the road and make up for lost time. We were totally desperate for a little getaway and decided that Connecticut would be the perfect place for us to explore.

Why Connecticut?

We chose Connecticut simply because it checked off all our criteria: within 5 hours from home, low number of COVID cases, and was likely to be empty from other tourists. But truthfully, we discovered Connecticut had so much more to offer. We found the landscape to be totally unique from other east coast states - at any given time, you can get from a sprawling city to the beach to woodsy hiking trails within 30 minutes. Our home state certainly can't offer that! Connecticut was friendly to drive in, easy to explore, and had tons of different options for activities. Whether you like to explore an urban area, get lost in the woods, or soak up the rich history via museums, Connecticut has you covered!

Must-See Road Trip Towns

We bounced up and down the coast during our getaway and picked out the top 5 road-trip worthy Connecticut towns. Each town has it's own special look and feel and together they offer up the unique Connecticut bundle of city, coastline, and country! Make sure you don't miss these 5 towns on your next drive through the Constitution State (really, that's what it is).

  • Bethlehem

  • Norwalk

  • New Haven

  • New London

  • Stonington (Mystic)

Bethlehem, Connecticut

This woodsy little town can be found in the mid-western section of the state in Litchfield County (unrelated to OITNB, I checked!) and is the perfect country escape. The whole town seemed to be out of a movie, down to the men in flannel shirts and overalls driving their tractors down the unpaved roads. Emphasis on unpaved roads. Oh yeah, and the cell/GPS reception is a little spotty so maybe make sure you have a general idea of your route before you head off in your car. We spent our nights in a sustainable off-grid geodesic dome (could that sentence be more millennial?) and our days hitting the trails.

There are some great hiking spots all over the surrounding area - and get this - amazing food, too! We were so surprised by how "out there" we were, yet how close we still were to civilization. If the image of roughing it at a glamp site is a little intimidating, don't worry, you can choose to spend your time antiquing on the famous Woodbury Antique Trail or experiencing one of the area's wineries.

Norwalk, Connecticut

Norwalk and surrounding area should be considered a must-stop for anyone looking to experience a little more hustle and bustle. You can feel the energy of New York here, and rightly so, because Norwalk is actually considered to be a part of the New York City metropolitan area. It's a short train ride into the city and from what we experienced, seems to be home to a lot of NYC-commuters. Don't get distracted by the honking cars and faster pace though, Norwalk has a lot more to offer than just NYC energy.

Norwalk is one of the most interesting cities we've ever experienced because we stayed in the suburbs, were able to drive into the high rise area for coffee every morning, and then hit the beach 10 minutes later. We've never seen an area that can accommodate so many different geographical elements into one small area and it's certainly interesting to experience! There's also a famous cemetery, walking trails, and the Lockwood Matthews Mansion, a national historic landmark.

New Haven, Connecticut

We just had to stop in New Haven to check out Yale University (anyone else have the Ivy League campuses on their bucket list??), and it didn't disappoint! Yale's campus is gorgeous and large enough to take up your whole day exploring. We highly recommend this stop for anyone interested in architecture, landscape photography, or history. There are plenty of museums to explore as well, plus the city itself.

This is also a must-stop for any foodies! New Haven has an incredible food history and you can try some historic classics like the first hamburger sandwich (in the world!) from Louis' Lunch and legendary pizza from Sally's Apizza that's rumored to have been frequented by Frank Sinatra. If you're looking for more details on how these places measure up, make sure you check out our Connecticut Food Tour!

New London, Connecticut

Our next stop takes you farther north into what we felt was the "start of New England." New London really had a different feel from the rest of the cities we visited, and we could tell right away this coastal town was proud of their differences. New London was put on the map for it's intense submarine and whaling history of the 19th century. This once-thriving town is a bit of a ghost town of what it used to be, but with all the bones to back it up. Take a walk down the old main street and appreciate the building facades, and read about the town's history down by the train station.

Don't leave without grabbing coffee and a treat from Muddy Waters Cafe, a famous spot with the locals, where you can cozy up in a chair with a hot latte and enjoy the atmosphere. For those that have worked up an appetite, you have to stop at Captain Scott's Lobster Dock, which is famous nation-wide for it's amazing seafood. Seriously, don't miss out on this hidden spot!

Stonington, Connecticut

The last stop on our tour might just have to be our favorite! You may have heard of the famous water-front town Mystic, which is actually smack-dab in the middle of Stonington Borough. If you're looking for a complete guide to Mystic, check out our travel guide here! Long story short, Mystic is an absolute must-see for it's quintessential New England charm, but it offers so much more too (think paddle boarding!). When you're done shopping and enjoying Mystic, drive about 15 minutes north to Stonington Borough.

Stonington offers its own cute and quiet water-front town, which you can likely explore without rubbing shoulders with any other tourists! Stonington is Mystic's best kept secret and we're here for it. Explore the tiniest lighthouse you've ever seen and go to Stonington Point, where you can see Rhode Island and New York from the beach!

Don't forget to pin this article so you can plan your Connecticut Road Trip!