Top 15 Attractions and Activities in Wilton, CT

This small town of just under 20,000 residents is located on Fairfield County’s prestigious Gold Coast.

In alignment with its affluent location, Wilton integrates luxurious residential neighborhoods with the offices of prominent international corporations, including Deloitte & Touche, Breitling, Sun Products, and ASML.

Historically rich, the Wilton Historical Society & Museum offers over 300 years of history to explore, showcasing an entire campus of 18th and 19th-century structures.

Additionally, the Weir Farm National Historic Site conserves the rural retreat of the artist J. Alden Weir.

Within this picturesque estate nestled in forests and meadows, visitors may traverse the paths once frequented by some of America’s most celebrated artists.

Let’s examine the top attractions in and around Wilton, Connecticut:

1. Weir Farm National Historic Site

One of only two National Historic Sites in the United States dedicated to visual arts, Weir Farm serves as the countryside home and studio of distinguished Impressionist J. Alden Weir (1852-1919). The artist referred to it as the “Great Good Place.” Situated on 60 acres of serene landscapes, it was frequented by prominent figures from the American Impressionist movement including Childe Hassam, John Singer Sargent, Albert Pinkham Ryder, and John Twachtman.

Following Weir’s passing, sculptor Mahonri Young, accompanied by Weir’s daughter, made it their residence, later joined by artist Sperri Andrews, a colleague of Young.

Among the 16 structures on the grounds, three significant buildings—the Weir House, Weir Studio, and Young Studio—exhibit works from the Weir, Young, and Andrews families.

The Burlingham House Visitor Center Gallery also hosts contemporary artworks.

Visitors seeking inspiration may borrow art materials such as paper, pencils, and pastels (and watercolors on weekends) from the Visitor Center porch.

2. Weir Pond

This four-acre pond was commissioned by J. Alden Weir in 1896, constructed with prize money awarded from his exhibition at the Boston Art Club. He built a boathouse on the northwestern shore, primarily using the pond for fishing and leisurely walks.

Historical photographs capture both Weir and John Singer Sargent by the water’s edge.

Later, Mahonri Young represented Weir Pond in two ink sketches.

A boathouse existed on the western shore for approximately 50 years until the 1960s, while Weir’s summerhouse on an island at the pond’s center has since vanished.

Today, the pond, surrounded by woods and rustic stone walls, serves as a lovely destination for artistic inspiration for those sketching and painting around the National Historic Site.

3. Wilton Historical Society & Museum

The Wilton Historical Society Museum Complex features a cluster of historic structures surrounding the red-painted Betts-Sturgis-Blackmar House, dating back to 1740. This complex also includes the Burt Barn Gallery (1840), the Sloan-Raymond-Fitch House (1770), the Abbott Barn (1860), a Blacksmith Shop built in 1890, and a two-seater outhouse from 1895. Visitors are welcome to explore these historic buildings, examine various antiquated tools displayed in the Abbott Barn, and stroll through the labeled Colonial Herb Garden dating back to 1750.

Both 18th-century residences are furnished to depict the evolution of New England domestic life from 1740 to 1910. Exhibitions, meetings, and lectures are hosted in both the Sloan House Gallery and Burt Barn Gallery, while a blacksmith is frequently available at his shop on Saturdays.

Hand-crafted gifts and toys can be found at the Betts Store.

4. Merwin Meadows Park

This community park is particularly vibrant from Memorial Day through Labor Day when the pond, beach, and accompanying bathhouse and pavilion/grills are accessible.

Lifeguards are on duty on weekends from May 25 until the end of the school year.

Subsequently, lifeguards patrol daily from 09:00 to 20:00 until the end of the summer break. Merwin Meadows Park welcomes both residents and visitors; however, a Park Pass is required for entry from late May until early September.

During the off-season, the park is ideal for families with young children, offering a playground and access to the scenic Norwalk River Valley Trail.

5. Norwalk River Valley Trail

Currently under development, the Norwalk River Valley Trail aims to connect Norwalk’s Calf Pasture Beach with Rogers Park in Danbury, traversing through Wilton, Ridgefield, and Redding along more than 30 miles of paths.

Wilton is already ahead, having established a nearly complete loop, with East Side and West Side trails along Route 7. The East Side provides a glimpse of what the Norwalk River Valley Trail will encompass: a three-meter-wide multi-use path composed of compacted stone dust, designed to be wheelchair accessible, extending approximately 2.25 miles between Wolfpit Road and Skunk Lane.

The West Side features the longest off-road segment, meandering through Merwin Meadows Park.

6. Woodcock Nature Center

Located on the border of Wilton and Ridgefield, the Woodcock Nature Center encompasses 149 acres of deciduous forest featuring hickory, oak, beech, and maple trees, along with ponds and wetlands.

The center offers after-school programs, summer camps, and various activities, while also serving as a no-cost visitor attraction.

The main building houses habitats for a variety of rescued animals, including a barred owl, a red hawk, a great horned owl, a spotted salamander, as well as multiple species of snakes, frogs, and turtles.

Outside, there are three color-coded trails available for exploration, with one featuring a boardwalk over the ecologically rich wetlands.

During Halloween, “un-haunted” hikes and hayrides are offered, alongside a Wreath Festival during the holiday season, as well as snowshoeing, cross-country skiing, and ice skating in winter months. Children are invited to welcome spring with an egg hunt.

7. Wilton Town Forest

The largest public green space within the town is Wilton Town Forest, an 188-acre area of rugged woodland that lacks facilities but offers navigable walking trails and paths for horseback riding.

The primary trail stretches 2.9 miles, also serving as a challenging route for mountain biking enthusiasts.

Predominantly deciduous, the forest features two fragrant hemlock groves that provide a delightful contrast.

Look for Sheep Falls in the northeastern section of the park, from which you can follow the beautiful Barrett’s Brook back to Branch Brook Road.

8. Hurlbutt Street School House

Since being included in the National Register of Historic Places, this single-story clapboard schoolhouse has remained intact since its establishment in 1834. The Hurlbutt Street School House is constructed on a wooden frame, featuring triangular gables at each end.

A quaint cupola housing the school bell is positioned above the entrance, with many original elements such as the blackboard, wood-burning stove, and educational charts preserved inside.

A historic privy remains intact outside the structure.

The school ceased operations as an educational institution in 1935 and subsequently came under the ownership of the Wilton Ladies Auxiliary, which evolved into the Hurlbutt Street School House Inc.

Today, the building serves as a living museum, primarily catering to school groups seeking a glimpse into historical education.

9. Gallaher Mansion and Cranbury Park

In the early 1930s, industrialist Edward B. Gallaher constructed this Elizabethan-style mansion adorned with elegant walnut paneling, a slate roof, intricate limestone coat of arms, and beautifully leaded windows in decorative mullions.

Despite being built during the Great Depression, Gallaher ensured his home included modern amenities such as an elevator, call buttons, an intercom system, and an incinerator.

Now available for event rentals, the mansion is situated within almost 220 acres of landscaped grounds open to the public.

Within the park, visitors can enjoy a well-appointed sculpture garden, a stone terrace, and a sprawling great lawn.

Numerous trails facilitate exploring the park, in addition to a frisbee golf course and a sizable playground for children.

10. Silvermine Guild Arts Center

New Canaan, particularly the Silvermine area, has maintained an artistic heritage since sculptor Solon Borglum (1868-1922) established his studio there in 1906.

In due course, a community of artists gathered at the studio to critique each other’s work, sometimes in stern terms. This community eventually evolved into the Silvermine Guild, officially founded in 1922. Esteemed artists such as Helen Frankenthaler and Milton Avery have exhibited here, and the New York Philharmonic has performed on the Arts Center’s grounds.

The Silvermine School of Art enrolls over 4,500 students each year across a diverse range of classes and workshops.

The center features five galleries hosting contemporary art exhibitions, regional juried competitions, and community programs encompassing film screenings and lectures.

The gift shop offers top-quality arts and crafts sourced from throughout the United States.

11. The Glass House

This captivating example of Modernist architecture is an essential stop in New Canaan.

Designed by Philip Johnson (1906-2005), an admirer of Ludwig Mies van der Rohe, the Glass House (1948-49) serves as a weekend retreat.

This study in geometry and proportion features transparent glass walls from floor to ceiling held by a steel, charcoal-painted frame. The bathroom, housed in a brick cylinder, is the only space obscured from view.

Encompassing 47 acres, the estate includes 13 additional Modernist structures, such as the Brick House (1949-50) where guests frequently stayed.

Johnson shared the estate with his lifelong partner, art critic David Whitney, who curated the landscaping and collected much of the art displayed on site.

Visitor tours commence from the Visitor Center in New Canaan, offering a basic one-hour visit to the Glass House or an extended two-and-a-half-hour tour of the estate on weekends.

12. Devil’s Den Preserve

The largest and most frequented nature preserve in Fairfield County is conveniently located near Wilton.

Visitors can easily spend half a day exploring the trails in this 1,756-acre area and still feel like there is much more to discover.

Over 500 varieties of trees and wildflowers, along with more than 140 species of birds, have been documented within Devil’s Den.

With 20 miles of trails, visitors can experience stunning features including the panoramic Great Ledge, the ravine and rocky cascade at Ambler Gorge, the Saugatuck Wildlife Refuge marshlands, and the historic Godfrey Pond, dammed for milling in the 1700s.

13. Wilton River Park Shopping Center

Situated to the south of the town library, this outdoor shopping center boasts an appealing vintage ambiance, featuring a diverse array of predominantly local shops, eateries, and a Bow Tie Cinemas location.

Noteworthy among the shops is Goldenberry Gourmet & Gift, which offers rare specialty items from across Europe and the British Isles.

Wilton River Park has also emerged as a premier dining destination, showcasing Mexican cuisine (Cactus Rose Cantina), pan-Asian fare (Happy Wok), Italian dishes (Tom E Toes Restaurant & Pizza), and contemporary American fare (Craft 14 Kitchen + Bar).

14. Wilton Playshop

Typically, four productions are staged annually at this volunteer-operated, nonprofit community theater.

Wilton Playshop has a rich history dating back to 1937 and continues to provide entertainment for the local community, along with educational opportunities for participants on and off stage.

Recent productions have included classics such as Philadelphia Story, Evita, Chicago, West Side Story, and The Lion in Winter.

Separate from the regular season is the Applause Series, which features live music, readings, and works in progress among other performances.

During intermission, patrons are invited to the Green Room for refreshments and to interact with cast members and the production team.

15. Ambler Farm

This historic 200-year-old farm is owned by the Town of Wilton and offers a variety of educational programs and events throughout the year suitable for all age groups.

Activities encompass beekeeping, sheep shearing, maple syrup production, cooking classes, and gardening workshops.

A highlight on the annual calendar is Ambler Farm Day, a fall festival held in late September, featuring a pumpkin patch, opportunities to interact with farm animals, an apple slingshot, a trebuchet for launching pumpkins, hayrides, and a make-your-own scarecrow station.

From June to October, the farm stand offers a rotating selection of fresh produce, including lettuce, basil, arugula, kale, fennel, cucumbers, carrots, sweet onions, baby leeks, summer squash, as well as the farm’s renowned maple syrup.