A Guide to Madison, Connecticut

Madison, Connecticut is a small but vibrant town on the Connecticut Long Island Sound shoreline, located halfway between New York City and Boston. Its small size makes it easy to miss, but Madison is one of the best beach towns in the United States, and you do not want to miss everything it has to offer. I recently spent a week in Madison with my mom and my sister, and this laid-back beach town was the perfect location for a relaxed, fun, family vacation. From sunbathing at the beach to exploring the  picturesque Main Street, Madison has everything you need to soak up the sun and relax during the summer.

Where To Stay:

My family rented a beachfront house on Kelsey Drive through Realtor.com, but you can also do so through Airbnb. I would highly recommend renting a house. We felt at home in our rental, and it gave us far more privacy and space than a hotel room would have. In our house, we could sunbathe on our porch or on the beach, cook meals in our kitchen and eat them outside, and watch movies and relax at night. We also had a beautiful view and access to a private community beach.  However, if you’re really attached to staying in a hotel rather than a rental, I’d recommend the Madison Beach Hotel, which is located directly on the beach.

The view from our rental house

Where To Eat:

The Wharf Restaurant

The Wharf Restaurant is a seaside restaurant with a beautiful view and fantastic seafood. My mom and I ordered a dozen oysters and devoured them in minutes. We loved them so much that we ordered another plate, adding up to a grand total of twenty-four oysters. It was expensive but well worth it. If you’re going to be overly indulgent, this is the place to do it. Although they’re known for their seafood, their pasta is just as delicious; I ordered the beet and goat cheese gocce, and I loved every bite.

The Chamard Vineyard

The Chamard Vineyard is a wonderful French bistro-inspired restaurant for a special occasion. I chose to spend my birthday dinner there, and I was not disappointed. While driving onto the grounds of this vineyard, I was floored by its beauty. I felt as if I was driving through the French countryside. I would highly recommend sitting outside so that you can properly appreciate the breathtaking view, but head inside once the sun sets—the mosquitos get vicious at night. The food is just as marvelous as the scenery—we split the charcuterie board and camembert as appetizers and loved them. For entrées: I ordered the gnocchi, and my sister ordered the croque madame. We were both fully satisfied, but of course, we left room for dessert. The chocolate pot de creme was the star of the night, but my mom’s creme brulée was a close second.

The gnocchi and croque madame


For a more casual meal, Moxie is a fantastic option. Located on Main Street, Moxie offers a modern twist on traditional meals. The ambiance is cozy but fun, and there is an outdoor bar that’s reminiscent of a tropical beach resort. The cocktails are creative, delicious, and fruity. We ordered a parmesan-garlic monkey bread as an appetizer, and it came topped with a homemade mixture of goat cheese and truffled mascarpone that blew the entire table away. My entrée was a delicious cheeseburger. Overall, Moxie is an excellent location for a laid back, lively meal.

The parmesan-garlic monkey bread

Ashley’s Ice Cream & Yogurt

On the way home from Moxie, we stopped by Ashley’s Ice Cream & Yogurt. This retro ice cream shop serves different homemade flavors every day. Although the line was a bit long, the ice cream was well worth the wait. Outside, we met an enormous, adorable dog, whose owner brings her here once a week for a treat. We spent about ten minutes petting the dog and talking to her wonderful owner. This interaction truly speaks to the gregariousness and openness of Madison locals—it’s not hard at all to make a friend here or find someone to talk to.

My ice cream at Ashley’s

Where To Go:

The Beach

I spent most of my time in Madison on the beach, and I recommend that you do the same. Which beach is the best depends on what type of experience you want.  Surf Beach Club is a lively and great for families—it comes equipped with a lifeguard, a basketball court, and a volleyball net. But for a quieter, more relaxing beach day, go to East Wharf of West Wharf , and you’ll be far less likely to be interrupted by screaming children.

Main Street

Main Street is filled with small, locally-owned boutiques. bellaPerlina is a standout, selling beautiful handmade jewelry. Madison Art Cinemas, a small but well-kept movie theater that primarily shows independent films, is another gem. The standout of Main Street is RJ Julia Booksellers. If you were to walk by RJ Julia, you would never guess that it was such a distinguished bookstore. Small and unassuming, RJ Julia is a store you can walk into to casually look around—but don’t miss out on its wonderful events. It hosts multiple book clubs, workshops for children and teens, and even yoga classes. You can also find many prominent published authors here, doing interviews and book signings.

Into the Big City:

Madison is located halfway between New York City and Boston. My family and I went into New York City for a day to see a Broadway show, and it was one of the highlights of the trip. Madison is the perfect place to enjoy the leisure of a small town, but the hustle and bustle of the big city isn’t far.   Madison, Connecticut feels like a town out of a dream. The people are friendly and kind, the beaches are relaxing, and the town is vibrant. Kids love it, parents love it, and as a twenty-one-year-old college student, I loved it too. If you’re looking to unwind and enjoy the summer sun, Madison is your location.

Bella Ross

I am a student at Emory University studying Creative Writing and Dance. I live in Atlanta, GA.