Among the New England states, Connecticut often goes unnoticed in terms of travel destinations. It may not have the expansive national parks of Maine, the celebrity appeal of Cape Cod, or the quirkiness of Rhode Island. However, Connecticut is home to charming towns that are perfect for weekend road trips. One such town is Madison, located on the southern coast of Connecticut’s Long Island Sound. As a suburban area of New Haven, Madison was named after James Madison by a wealthy sea captain, despite the fact that Madison had no ties to the state. With a population of 17,000 spread across a compact 36 square miles, Madison offers a vibrant and welcoming downtown area, sandy beaches, and easy navigation.
Getting to Madison, Connecticut is fairly straightforward. It is approximately 16 miles east of New Haven and 38 miles south of Hartford. Most points in the Hudson Valley can reach Madison by car in about 2 ½ hours. Travelers from the mid and lower Valley can take I-84 East, CT-25 South, and I-95 North. Those coming from points north can take I-90 East to I-91 South and CT-81 South.
Day 1 in Madison can be filled with shoreline activities, self-care, and entertainment. Kickstart your morning at Cohen’s Bagel Company, known for its wide variety of bagels that rival those found in Manhattan or Brooklyn. Try their Avocado Smash, a delicious combination of mashed tomato and avocado on a jalapeno or “cheddar everything” bagel.
Next, visit Hammonasset Beach State Park, a popular attraction featuring two miles of beautiful beach, camping facilities, and a nature center. Kids will enjoy searching for seashells along Meig’s Point, where an abundance of shells from various species get washed ashore. After soaking up some sun, head into downtown Madison, just 2 ½ miles away.
For lunch, stop by Life Bowls, a health-focused eatery offering smoothies, acai and pitaya bowls, salads, and toasts. Try their Maui Wowie bowl, packed with nutritious ingredients like acai, blueberries, pineapple, goji berries, and shredded coconut. If you still have room for dessert, Ashley’s Ice Cream is a must-visit, serving delightful frozen treats made with a creamy custard base. Don’t forget to book a post-lunch spa treatment at one of Madison’s top-rated spas, such as Celtic Healing Arts, Aroma Massage, or Jennie Fresa. Aria Dermspa provides medical aesthetic treatments in a serene environment.
When it comes to dinner, note that most restaurants in Madison close their dinner service at 9 p.m., so it’s best to dine early. Steamed, located on Boston Post Road, offers a variety of Chinese dumplings, noodles, buns, and boba tea. Jia Mei Asian Kitchen on Wall Street has an affordable selection of Chinese soups, stir-fries, rice dishes, and Thai curries.
In the evening, enjoy a show at Madison Lyric Stage, a professional theater company situated on the historic grounds of Deacon John Grave House. They showcase musicals, operas, plays, and concerts. Alternatively, you can relax and watch a first-run or vintage movie or catch a live-broadcast opera at Madison Cinemas.
Day 2 offers a chance to explore nature, history, and downtown shopping. Begin your day at Rettich Preserve, an 11-acre area filled with woodlands and meadows adorned with wildflowers near the Hammonasset River. It’s best to visit this location in the early morning or evening before the traffic intensifies on nearby I-95. Return to town and grab breakfast from Meriano’s Bake Shoppe, a family-owned bakery known for its delectable Italian pastries like sfogliatelle, pasticiotti, pignoli, and the unique lobster tail, which combines Naples and New England flavors.
Take a leisurely stroll through the Madison Green Historic District, a town green surrounded by historic buildings. While typically open on Wednesdays, the Allis-Bushnell House, constructed in 1785, occasionally offers weekend programming, allowing visitors to experience different periods of American history. Don’t miss the beautiful perennial gardens.
For lunch, you can find food trucks parked near the Madison Youth & Family Services building on School Street. RJ Café Bistro offers classic sandwiches like curry chicken salad and turkey and avocado. Madison Cheese Shop & Café caters to both vegetarians and meat lovers, serving gourmet grilled cheeses, cold sandwiches, cheese boards, and charcuterie.
After your meal, explore the downtown area and visit RJ Julia Booksellers, a sizable bookstore offering a wide range of fiction and nonfiction titles. Water Street Jewelers presents artisanal and luxury jewelry collections, as well as custom designs. If you’re a bird enthusiast, stop by the Audubon Shop for squirrel-proof bird feeders and other supplies, including optical birding equipment. Along Wall Street, find Robertson Madison for designer casual clothing and the Wine Thief for an impressive selection of globally sourced wines, particularly French grapes.
As the sun begins to set, make your way to Wharf Beach and take a stroll along the flagstone pier, where you can admire the boats gracefully floating in the ocean. Experience the beauty of the coast while sipping a refreshing cocktail on the grand wraparound porch of The Wharf at Madison Beach Hotel. For a memorable dinner, visit Café Allegre, a chef-owned restaurant known for its contemporary Italian dishes. Indulge in the arugula salad with a creamy wheel of burrata, pomegranate seeds, and peaches, or opt for the capellini with lobster in a tomato cream sauce. Don’t hesitate to ask for the stuffed, fried artichoke, even if it’s not listed on the menu.
When it comes to accommodations in Madison, be aware that most lodging options, including short-term rentals, tend to start at $250 per night during the high season. If you prefer outdoor experiences or have a tighter budget, consider camping at Hammonasset State Park or renting a cozy cottage in nearby Clinton. For a well-thought-out and comfortable stay, try The Homestead, offering spacious rooms with modern bathrooms, convenient amenities like multiplug units and USB ports, in-room record players, free-choice snacks, outdoor seating areas with fire pits, and a complimentary self-serve breakfast. Alternatively, Hilton Curio’s Madison Beach Hotel provides ocean views, nautical-inspired rooms, and a spa for ultimate relaxation.
Whether you’re seeking a weekend getaway or a new destination to explore, Madison, Connecticut offers a delightful blend of natural beauty, historic charm, and vibrant downtown experiences.
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