Top 15 Attractions and Activities in Madison, Connecticut

Only 15 miles east of New Haven, Madison is a historic oceanfront town characterized by centuries-old architecture and extensive public shoreline.

At Hammonasset Beach State Park, visitors can relax along the picturesque Long Island Sound or observe wildlife along trails in protected woods and marshland.

Madison encompasses much more than its shoreline, featuring a charming, pedestrian-friendly downtown with locally-owned shops, restaurants, and entertainment options that attract visitors.

One of the nation’s most acclaimed independent bookstores resides here, alongside an art cinema with a rich history dating back to 1912.

Let’s delve into the premier activities available in and around Madison:

1. Hammonasset Beach State Park

The largest coastal park in Connecticut spans nearly 1,000 acres of beach, marshland, and coastal woodland located southeast of Madison Center.

With two miles of natural sandy beach, complete with a boardwalk, the park accommodates visitors, ensuring that it does not feel overcrowded, despite being one of the state’s most popular attractions.

The beach serves as a significant nesting ground for piping plovers, and certain areas may be cordoned off during the summer months.

Bicycles are available for rental until Labor Day, allowing exploration along a network of shaded trails.

The park also features a campground with over 500 units and the Meigs Point Nature Center, which offers insights into the park’s diverse ecology.

2. Meigs Point Nature Center

Located at Hammonasset Point, this environmental education center was inaugurated in 2016, showcasing various exhibits that highlight the diverse wildlife inhabiting different habitats along the Connecticut shoreline, ranging from the beach to the skies, woods, and water.

A small collection of live animals is on display, all of which have been rescued and are unable to be returned to their natural habitats.

Visitors can view turtles, amphibians, fish, crabs, and snakes, with a touch tank featuring horseshoe crabs designed for children.

The center hosts activities such as canoe trips, bird walks, sustainable art and crafts, environmental awareness workshops, scientific experiments, stargazing, and beachcombing.

3. Madison Green Historic District

Madison Green has its origins in 1705, serving as the location for a meeting house for what was then known as East Guilford.

As a result, the green evolved into a village center and later a town center following Madison’s incorporation in 1826. This historic district has been listed on the National Register of Historic Places since 1982 and features an array of beautiful architecture in its vicinity.

Along the Boston Post Road, one can find an array of 18th and 19th-century houses, with the Deacon John Grave House situated further east. Scattered around the green are notable structures including the Lee Academy (1821), Academy Elementary School (1884), a community meeting building (1884), Memorial Hall (1896), and, most impressively, the First Congregational Church erected in 1838. Continuing east along the Boston Post Road leads to Madison’s charming commercial center, which is highlighted by various independent businesses.

Concerts are held on the green every Sunday at 6:00 PM from the beginning of July until the end of August.

4. Deacon John Grave House

This colonial-era Saltbox house stands as one of the oldest structures in Madison, with its construction dating back to 1681. It is named after John Grave I, a deacon at the first Guilford meeting house and a town clerk in Guilford.

The house was actually constructed by his son John II, who operated a tavern on the site during the early 18th century.

Incredibly, the house remained home to a continuous line of Grave descendants until 1933. A peculiar feature of the Deacon John Grave House is a secret compartment located in the attic behind the chimney, the purpose of which continues to elude explanation.

The house does not maintain formal operating hours, but it opens for specific events, such as a summer 2019 production of Into the Woods by the Madison Lyric Stage.

Arrangements can be made for guided tours by appointment, catering to groups and individuals.

5. R.J. Julia Booksellers

Recognized as one of the premier independent bookstores not only in Connecticut but across the nation, R.J. Julia was established in Madison Center in 1989. The store embodies the charm of large independent bookstores with friendly and knowledgeable staff, alongside an extensive and diverse collection of titles.

This venue has also become a popular stop for prominent authors on book tours, with notable visitors including Hillary Clinton, Anne Rice, and Jane Fonda over the past 30 years.

A dedicated wall displays signed photographs of important visitors. Like many contemporary bookstores, R.J. Julia features a café/bistro offering light meals and sweet treats.

6. Madison Art Cinema

Another cherished institution in Madison, this intimate cinema showcases first-run independent and domestic films, while also hosting community events and fundraisers from local organizations.

The establishment dates back to 1912 when it initially opened as the Bonoff Theatre.

Originally a single-screen venue, it was expanded to include a second auditorium after being acquired by Hoyts Theatres in 1977. Over its century-long history, the building has served diverse purposes, including a gymnasium and meeting hall, with a basketball court still located beneath the sloped wooden floor.

Madison Art Cinema is equipped with a state-of-the-art sound system (Dolby Digital, featuring JBL speakers), complemented by an opulent interior that showcases an eye-catching color palette of aquamarine, antique gold, and a red tone referred to as “Ming Red.”

7. Rockland Preserve

Over the past decade, this rugged 650-acre natural area situated in northern Madison has transformed into a haven for mountain bikers.

The Singletracks of Rockland provide an undulating tour of the terrain, featuring exciting elements crafted through countless hours of volunteer effort.

The preserve offers 17 trails, varying in difficulty from easy (green circle) to exceedingly challenging (double black diamond). A GPS map is accessible on the Madison Town website to facilitate navigation, and a basic code can be found at each trail entrance.

8. Henry Whitfield State Museum

This historic residence in Guilford transports visitors back to the earliest days of European settlement in Connecticut.

Constructed from local granite, the Henry Whitfield House has stood since 1639, originally built for the namesake Puritan minister who played a key role in founding the town.

As the oldest house in the state and the oldest stone dwelling in New England, it historically served as a refuge for residents during the tumultuous early settlement years.

The Visitor Center hosts rotating exhibits about this period, and guests can partake in guided or self-guided tours of the house, adorned with artifacts from the 17th to the 19th century.

The grounds feature centuries-old stone walls, a bronze statue of Whitfield, and a genuine ship’s cannon dating from the War of 1812.

9. Chamard Vineyards

At Chamard Vineyards, visitors can enjoy a winery and bistro amidst a picturesque landscape.

The vineyards are meticulously maintained, cultivating varietals such as Cabernet Sauvignon, Cabernet Franc, Pinot Noir, Merlot, and Chardonnay for their unique wines.

Benefiting from the moderating influence of Long Island Sound, located just two miles away, the vineyard’s grapes flourish.

The tasting room welcomes visitors from Tuesday to Sunday, and winery tours can be arranged by appointment.

The bistro, with a capacity of 35, features a French-inspired farm-to-table menu offering dishes like croque madames, pan-roasted organic chicken, spring-roasted lamb loin, or steak frites.

10. The Shoreline Greenway Trail

A collaborative initiative aimed at enhancing shoreline accessibility for walkers, wheelchair users, and cyclists, the Shoreline Greenway Trail is still in its early stages of development.

Currently, three miles of safe, off-road trails are available, with the most popular segments located in Madison.

The Hammonasset segment extends just over a mile and ranks among Connecticut’s most traversed walking and biking paths.

This trail provides essential access to Madison while diverting users away from the hazardous Boston Post Road (Route 1), which parallels the shore.

Tree cover blankets most of the path, offering occasional breathtaking views of the sound and the park’s shimmering marshes.

11. Clinton Crossing Premium Outlet

This outdoor shopping center mimics the charm of a quaint New England village, where visitors can find discounts of up to 65% from over 70 designer brands behind clapboard storefronts.

For reference, premium clothing brands available include Polo Ralph Lauren, DKNY, Saks Fifth Avenue, Calvin Klein, Tommy Hilfiger, Michael Kors, alongside midrange favorites and sports brands such as Gap, American Eagle, Levi’s, Abercrombie & Fitch, Nike, Adidas, Asics, New Balance, and Under Armour.

Jewelry and accessory options include Kay’s Jewelers, Swarovski, Fossil, and Sunglass Hut, in addition to cosmetics available at Luxury Beauty Store and Fragrance Outlet, as well as high-end cookware from Le Creuset.

Visitors can also enjoy a treat or two from Ben & Jerry’s or soft serve from Carvel.

12. The Audubon Shop

The Connecticut shoreline is renowned for bird watching, and Madison is home to what is considered the premier store for birders in the Northeast.

In addition to offering a diverse range of books, maps, and equipment such as binoculars, telescopes, tripods, and accessories, the Audubon Shop serves as a cornerstone of the birding community in Madison, organizing guided walks throughout the year.

The fall migration marks a particularly exciting time to visit, allowing participants to join experts at Hammonasset Beach State Park to observe migrating eagles, hawks, songbirds, waterfowl, and shorebirds.

During the winter months, visitors can spot bald eagles from Canada hunting along the Connecticut River.

13. Scranton Memorial Library

Established in 1901 through the generous donation of affluent resident Mary Scranton, the town’s public library continues to serve as a vital community resource.

The Scranton Memorial Library houses approximately 114,000 volumes, drawing an average of 360 visitors daily.

Following an expansion 30 years ago, the original Renaissance Revival structure now accommodates a fantastic children’s department.

As a local staple, the library hosts over 850 programs annually, targeting all age groups, particularly young children through workshops, storytimes, and more.

For adults, it remains a tranquil space to work, featuring free Wi-Fi and public-use computers.

14. Surf Club Beach

Despite its name, Surf Club Beach welcomes the public and features an inviting 365-meter stretch of golden sand.

The surrounding park spans 45 acres and adjoins a tranquil residential neighborhood and Madison Country Club.

Facility offerings include playgrounds for children up to age 12, basketball courts, athletic fields, bocce courts, horseshoe pits, sand volleyball courts, a concession stand open during summer, and a launch area for kayaks and sailboats.

As with various municipal beaches in Connecticut, seasonal passes are required, although they are limited to residents.

15. East Wharf Beach

Similar restrictions apply during summer at another pleasant beach characterized by a sandy shore interspersed with rocks, protected by wooden groynes.

East Wharf Beach features a rocky point extending into the sound to the east, making it an ideal site for early risers to witness sunrises (no passes required during those hours!). A gazebo provides a picturesque spot for picnics while enjoying the scenic views, along with an access point for rooftop boats.