A Southern Connecticut Road Trip: Norwalk, Bridgeport, and New Haven

My husband Mike and I love a good road trip, and a holiday weekend makes for a great excuse to hit the road! Our most recent adventure was a fantastic visit to southern Connecticut over Presidents Day weekend. More specifically, we visited the lovely cities of Norwalk, Bridgeport, and New Haven, all of which are fabulous.

And even if you don’t have a car, any New Yorker can hop on Metro-North to visit these great cities, which are all within a two-hour train ride from Manhattan. Read on for more ideas on what to see and what to do for a low-key and relaxing weekend in southern Connecticut!

When to Go

Being near the water, southern Connecticut is obviously going to be an excellent choice for a warm-weather visit. However, as with many coastal towns and cities, the warm weather also brings out larger crowds, higher hotel prices, and a whoooole lot more traffic, which can make an off-season visit seem a bit more appealing. 

And if you’re open-minded and flexible with your plans, you can enjoy off-season visits to tons of places you might never dream of setting foot in during the high season. So don’t let the cold weather deter you this winter, and consider a visit to southern Connecticut!

Norwalk Connecticut
Beautiful Norwalk, CT homes as seen by boat!

Where to Stay

We stayed at the Norwalk Doubletree, which had lots of diners, big box stores, and even a Bowlmor nearby. It was comfortable and affordable and located right off of I-95, making it easy to get everywhere we needed to go. We’re usually more practical when selecting where to stay, but if you’re looking for something more on the cute and quaint side you might want to consider something more like the Guest House at the Norwalk Inn, the Westport Inn, or the Delamar in Southport. No matter where you stay in the area, you’ll likely need to drive to the various local attractions, so pick a place that best suits your needs, style, and price point.

What to Do

  • Stroll through SoNo: South Norwalk, otherwise known as SoNo, is not what it once used to be. Rumor has it the area used to be a bit on the seedier side, but development over the past decade has brought in trendy bars and restaurants, condos, and high-end shopping, all alongside the Norwalk River. There is plenty to see and do here, and we enjoyed checking out all the various bars and restaurants, peeking into shops, and strolling along the river.
  • Maritime Aquarium: If you’re spending time in SoNo, you won’t want to miss the fabulous Maritime Aquarium, which is right on the Norwalk River. It looks small from the outside, but they had an incredible variety of critters inside. My personal favorites were the jellyfish and sharks! Oddly enough, they also had some meerkats, owls, and other animals you wouldn’t normally associate with an aquarium. There’s an IMAX theater if you’re into that kind of thing and all kinds of fun playspaces for the kiddos if you bring them along for the trip.
Norwalk Maritime Aquarium
The Maritime Aquarium in Norwalk, CT
Waving Turtle
Pretty sure this guy was waving at me
Norwalk Aquarium Flounder
That’s some good camouflage!
  • Cruises: The Maritime Aquarium also offers various cruises, and we were happy to jump on board their Seal and Bird Spotting cruise, which took us out the Norwalk River and around the Norwalk Islands. We even caught a glimpse of the Manhattan skyline for a while! Later in the spring and summer, the seals go away but the cruises continue. The scenery is beautiful, and as we journeyed through the area, we loved seeing some of the private homes set upon the smaller islands. Our day was cold but very blue and sunny, and the complimentary coffee and hot chocolate offered on board kept us nice and toasty throughout the trip!
Norwalk Cruise Lighthouse
One of the many lighthouses we saw on our cruise. Check out that gorgeous blue sky, too!
  • Cushing Center Brain Museum and Tumor Registry: Once you make it to New Haven, you should visit Yale’s Medical Library to check out the Cushing Center’s Brain Museum, which includes a collection of brains and tumors that formed Dr. Harvey Cushing’s brain tumor registry. Cushing was a pioneer in the field of neurosurgery and dedicated his life’s work to studying the brain and nervous system. Without Cushing and his meticulous study of the brain, it’s hard to say how long it might have been before more advances were made in the field of neurosurgery. The museum is a little morbid but also utterly fascinating and worth a visit if you find yourself in New Haven. Also, it’s free!
Cushing Center Brain Museum
This tiny space and another little section off to the right encompass the entirety of the Cushing Center’s brain and tumor collection. In addition to the glass-topped cases, each of the drawers below can be pulled out to reveal even more items on display. We had the whole place to ourselves the day we visited!
Cushing Center Tissue Samples
Tissue samples on display at the Cushing Center
  • Yale University Tour: If you’ve never been to New Haven, a stop at Yale University is a must-do for your first visit. The school offers free public tours seven days a week, each led by a current Yale student. Lasting just over an hour, you’ll take a walk through the campus, where you’ll see a variety of quads, residence halls, and classroom buildings. You will also visit the Beinecke Rare Book & Manuscript Library, which houses a copy of the Gutenberg Bible, among other literary treasures, and has marble windows to filter out direct sunlight so as to prevent damage to the rare collection.
Yale University Old Campus
Old Campus is where Yale’s New Haven campus originated. Though the school was actually founded in 1701, it didn’t move to New Haven until 1716.
Sterling Memorial Library
This is the Sterling Memorial Library, designed by James Gamble Rogers. He wanted to build a cathedral, which Yale didn’t need.  Instead, he made the school a library that just looked like a cathedral instead!
Beinecke Rare Book and Manuscript Library
Inside the Beinecke Rare Book and Manuscript Library. Note the far wall which has marble squares instead of windows to prevent direct sunlight from damaging the library’s collection.
  • Yale Collection of Musical Instruments: While on campus, you may also want to pop in to see Yale’s Collection of Musical Instruments, many of which date back to the 15th and 16th centuries. Some of the instruments are unique and unusual, and others are simply gorgeous representations of the finest quality instruments of their time. I particularly enjoyed the second floor which houses the antique pianos and harpsichords! The exhibit is free with a $2 suggested donation.
Yale Collection of Musical Instruments
One of the more unique instruments in their collection!
Tiny Violins
Teeny tiny violins. Or something. The ones that look like they’re sideways actually aren’t. That’s just how wide they are!
Yale Instrument Pyramid Piano
How cool is this thing??? Modern instruments seem so boring in comparison.
  • Pez Visitor Center: In Bridgeport, you may want to find your way to the Pez Visitor Center. We didn’t personally make it here ourselves, but we saw a sign for it from the highway and were disappointed that we couldn’t squeeze it into our trip. It’s a self-guided experience, but they have interactive exhibits throughout to keep you entertained. If you visit during the week, you can also watch dispensers and candy being packaged in their production facility.
  • The Barnum Museum: I was disappointed that the Barnum Museum was closed on the weekends and we couldn’t visit, but if you’re in Bridgeport on a Thursday or Friday, the museum looks like a unique and intriguing place to stop. It’s housed in the last surviving building connected to P.T. Barnum and includes artifacts that belonged to Barnum and Tom Thumb.
  • Ferry to Port Jefferson: If a cruise around Norwalk isn’t satisfying enough for you and you’d like to take a more scenic journey back to NYC, consider taking your car onto the Bridgeport-Port Jefferson ferry. The ferry runs multiple trips daily across Long Island Sound, all year round. The trip takes about an hour and 15 minutes so it won’t save you any time getting back to the city, but it’s certainly a more interesting way to travel!
  • Closed for Winter: If you do visit the area during wintertime, you’ll find some local attractions are closed until spring. Here are a few spots in Norwalk that we missed on our trip but looked like they’d be worth checking out. If you want to add these attractions to your southern Connecticut visit, you’ll need to plan to visit starting in May and throughout the summer.

Where to Eat and Drink

We did most of our eating and drinking in Norwalk, primarily in the lovely SoNo area where Washington Street offers plenty of options to suit your fancy. Pretty much all of the places we passed had signs advertising both happy hour and late night happy hour, all of which featured discounted drinks, and many of which offered discounted appetizers, too!

  • Peaches Southern Pub and Juke Joint: If you’re looking for a decadent brunch option, Peaches Southern Pub and Juke Joint is it. We had biscuits and gravy and country-fried steak, both of which were fantastic. We got a little jealous, too, when we saw our dining neighbors receive an order of sticky monkey bread! They also have live music, so this place is good for evening dining and entertainment, too.
  • Driftwood Diner: I loved this bright and airy little diner situated near the Doubletree Hotel in Norwalk. Portions were decent but not enormous, and everything was delicious. If you want a yummy bite before jumping back onto I-95, Driftwood Diner is a good option!
  • Iron Brewing Company: We love to hit up the local breweries, and we found this one on Washington Street. They have a limited selection on tap, but all of Iron Brewing Company’s beers were decent. They also had a great guest cider on tap that I enjoyed for my dessert! What really stood out, though, was the food. My husband had the smothered fries, covered in chicken and beer cheese, and I had the hanger steak with the biggest mound of mashed potatoes I’ve ever been served. All of it was super yummy, and the giant burgers we saw coming out of the kitchen looked pretty amazing as well.
  • Bourbon Raw: Oh bourbon, how I love thee. So imagine my delight to discover this bar which offers more than 100 different bourbons. We visited during happy hour and enjoyed some of their $5 appetizers with our beverages. Bourbon Raw also has a “raw bar” which isn’t our thing so I can’t attest to its quality. We were pretty satisfied between the bourbon and appetizers we did have, though!
  • Bandido: If it’s a margarita or sangria you’re craving, swing by Bandido where both can be found on happy hour for $5. We had a drink here and enjoyed some chips and salsa, but we didn’t try anything else. It has excellent reviews on Yelp, though, so I’m a little sad we didn’t sample their food.
  • Mecha Noodle Bar: We did not eat here, but the Mecha Noodle Bar was PACKED every time we walked by it. If you’re into ramen or pho, this seems to be the place to go in Norwalk judging by their non-stop crowds. They also have happy hour and a very interesting cocktail list!
  • Donovan’s: During our boat cruise, a local couple told us that Donovan’s has the best clam chowder in the area. Once the sun set and it started getting colder, a little chowder sounded like just the right thing. And it lived up to the hype, leaving us both sad that we got only a cup instead of a bowl. Add a Guinness to the side and a burger or fish and chips, and you’re pretty well set!
Norwalk Donovan's Clam Chowder
The award-winning clam chowder from Donovan’s! Pairs nicely with a Guinness…
  • Two Roads Brewing Company: We’ve had Two Roads beer before in NYC, but we didn’t realize they were based in Connecticut. After seeing their billboard on I-95, though, we decided to stop by! Sadly, the place was overflowing, and people were lined up three deep to order at the bar. We do like their beer, so if you can catch them on a less busy day, it seems like it would be a fun place to hang out and enjoy a flight. 
  • Brewport: And if you’re interested in a brewery with a little less action, try Brewport in Bridgeport instead. They have a chill vibe and plenty of places to sit, so it was already a winner in our books. And not only did we enjoy all of their beer (I’m looking at you peanut butter chocolate porter!) but we loved their fantastic food as well. Their specialty is massive salads and pizzas, and we split one of each. They also make their own root beer on-site, and we topped off our delicious meal with a couple root beer floats. YUM. 
Brewport Connecticut Beer Flight
My delicious flight from Brewport. A stout and a porter on tap at the same time is a treat for a dark beer lover such as myself.

Norwalk, Bridgeport, and New Haven all have something to offer everyone, and we were delightfully surprised by how much we enjoyed our visit to these wonderful cities. So if the winter blues have got you down and you need a little weekend pick-me-up, hop in the car or jump on Metro-North and spend some time in southern Connecticut. And if you do go, stop back here and let me know how you liked your trip!

If you’re from the area or have visited before, let me know what other spots we should check out on a future visit!

Looking for another off-season road trip? Check out my road trip guide to the Hamptons!

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