15 Best Things to Do in Wilton (CT)

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

True to its location, Wilton blends plush residential areas with the headquarters of international corporations like Deloitte & Touche, Breitling, Sun Products and ASML.

There’s more than 300 years of history to investigate at the Wilton Historical Society & Museum, which looks after a whole campus of buildings from the 18th and 19th century.

Elsewhere, the Weir Farm National Historic Site preserves the country retreat of the painter J. Alden Weir.

On this bucolic property embedded in woods and meadows you can tread the path of some of America’s most celebrated painters.

Let’s explore the best things to do in and around Wilton, Connecticut:

1. Weir Farm National Historic Site

One of only two National Historic Sites in America dedicated to the visual arts, Weir Farm is the rural home and studio of the influential Impressionist J. Alden Weir (1852-1919). Described by the artist as the “Great Good Place”, Weir Farm is in 60 acres of idyllic woods, fields and streams, and was visited by luminaries of the American Impressionist movement like Childe Hassam, John Singer Sargent, Albert Pinkham Ryder and John Twachtman.

After Weir passed on, the sculptor Mahonri Young moved here with Weir’s daughter, followed by artist Sperri Andrews, a friend of Young.

Of the 16 buildings on the site, three – the Weir House, Weir Studio and Young Studio – display works by members of the Weir, Young and Andrews families.

There’s also contemporary art at the Burlingham House Visitor Center Gallery.

If you feel inspired you can borrow art supplies like paper, pencils and pastels (as well as watercolors on weekends) from the Visitor Center porch.

2. Weir Pond

J. Alden Weir ordered this four-acre pond in 1896, and it was built using prize money earned from the Boston art Club exhibition of his work. The Truants.

Weir built a boat dock on the north-western shore, and mainly used the pond for fishing and walks.

Archive photos show Weir and John Singer Sargent posing next to the water.

Later, Mahonri Young would depict the Weir Pond in two ink sketches.

A boathouse was on the western shore for around 50 years up to the 1960s, while a summerhouse built by Weir on an island in the center has long since disappeared.

Today the pond, wreathed in woodland and rustic stone walls, is a destination for a pleasant and source of artistic inspiration for people out sketching and painting around the National Historic Site.

3. Wilton Historical Society & Museum

There’s a huddle of historic houses at the Wilton Historical Society Museum Complex, set around the red-painted Betts-Sturgis-Blackmar House, which is in situ and dates to 1740. This is accompanied by the Burt Barn Gallery (1840), the Sloan-Raymond-Fitch House (1770), the Abbott Barn (1860), a Blacksmith Shop from 1890 and a two-seat outhouse from 1895. At the museum you’re free to tour these historic buildings, viewing all sorts of historic tools in the Abbott Barn and taking a turn in the 1750 Colonial Herb Garden, where all the plants are labeled.

Both 18th-century residences are furnished to give a timeline of New England domestic life from 1740-1910. There are exhibitions, meetings and lectures in the Sloan House Gallery and Burt Barn Gallery, and a blacksmith will often be in residence at his shop on Saturdays.

Drop by the Betts Store for hand-crafted gifts and toys.

4. Merwin Meadows Park

This community park really comes into its own between Memorial Day and Labor Day, when the pond, its beach and accompanying bathhouse and pavilion/grills are all open.

There are lifeguards on duty on weekends between May 25 and the last day of school.

From then until the end of the school break lifeguards are on patrol daily from 09:00 to 20:00. Merwin Meadows Park is open to both residents and non-residents, but you will need to get hold of a Park Pass if you want to come between late-May and the start of September.

Of course, at other times the park is a fine place to bring little ones to burn off energy at the playground, or to amble on a stretch of the Norwalk River Valley Trail.

5. Norwalk River Valley Trail

Currently under construction, the Norwalk River Valley Trail will link Norwalk’s Calf Pasture Beach with Rogers Park in Danbury, weaving through Wilton, Ridgefield and Redding on more than 30 miles of trails.

Wilton is ahead of the curve and already has a loop, mostly complete and with an East Side and West Side flanking Route 7. The East Side gives you a good idea of what the Norwalk River Valley Trail will look like when it’s ready: There’s a three-meter-wide multi-use path, laid with compacted stone dust and accessible to wheelchairs, meandering through woodland for around 2.25 miles between the intersection of Wolfpit Road and Route 7 and Skunk Lane.

On the west side, the longest off-road section bends through Merwin Meadows Park.

6. Woodcock Nature Center

Set on the boundary between Wilton and Ridgefield is an environmental education center in 149 acres of deciduous woodland, growing hickory, oak, beech and maple, bedded with ponds and wetlands.

The center provides after school programs, a summer camp and all sorts of other activities and events, but also serves as a free visitor attraction.

The main building has habitats for a host of rescued animals, among them a barred owl, a red hawk, a great horned owl, a spotted salamander and numerous species of snakes, frogs and turtles.

Outside are three color-coded trails to explore, one lifting you via boardwalk over the ecologically diverse wetlands.

At Halloween there are “un-haunted” hikes and hayrides, while there’s a Wreath Festival in the advent season, snow-shoeing, cross-country skiing and ice skating at the Winter Wonderland.

Later, children can welcome in spring with an egg hunt.

7. Wilton Town Forest

The largest public open space within the town lines is this 188-acre tract of rugged forest, free of facilities but navigable on walking trails and bridleways.

The main route is the 2.9-mile Blue Trail, also serving as a rather technical ride for mountain bikers.

The majority of Wilton Town Forest is deciduous, except for two fragrant groves of hemlocks that offer an agreeable contrast.

The main natural feature to look for is Sheep Falls, in the north-east of the park, and from there you’ll trace the picturesque Barrett’s Brook back to Branch Brook Road.

8. Hurlbutt Street School House

On the National Register of Historic Places, this single-story clapboard schoolhouse was raised in 1834. The Hurlbutt Street School House is on a wood frame, and has triangular gables at each end.

Above the entrance is a little cupola housing the school bell, while lots of original features survive inside, like the blackboard, wood-burning stove and a teaching chart.

Still intact outside is a historic privy.

The school house closed as a place of education in 1935, and was bought by the Wilton Ladies Auxiliary, which eventually became the Hurlbutt Street School House Inc.

The building functions as a living museum, mostly for school groups to experience education in days gone by.

9. Gallaher Mansion and Cranbury Park

In the early-1930s the industrialist Edward B. Gallaher built himself this Elizabethan-style mansion, with fine walnut paneling, slate roof, moulded limestone coats of arms and leaded windows in handsome mullions.

This was deep in the Great Depression, but Gallaher couldn’t be without modern conveniences like an elevator, call buttons, an intercom system and an incinerator.

Now a venue rented out for events, the mansion is in almost 220 acres of landscaped grounds, open to the public.

There’s a refined sculpture garden, a stone terrace, a sweeping great lawn.

You can experience the park on foot on a web of trails, and there’s a frisbee golf course and a large children’s playground.

10. Silvermine Guild Arts Center

New Canaan, or specifically Silvermine, has had an artistic bent ever since the sculptor Solon Borglum (1968-1922) moved here in 1906 and built himself a studio.

Before long a community of artists would meet at there to discuss each other’s work, often in harsh terms, and this group eventually became the Slivermine Guild, which was officially founded in 1922. Luminaries like Helen Frankenthaler and Milton Avery have featured in exhibitions here, and the New York Philharmonic has performed on the Arts Center’s grounds.

The Silvermine School Of Art has over 4,500 enrolments each year, for scores of classes and workshops.

There are five galleries hosting contemporary art exhibitions and regional juried competitions, community programs for film screenings and lectures.

The gift shop stocks high-quality arts and crafts from across the United States.

11. The Glass House

This mesmerising piece of Modernist architecture is a necessary detour in New Canaan.

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

A study of geometry and proportion, the building is walled with transparent glass windows from floor to ceiling on a steel, charcoal-painted frame.

The only space occluded from the outside is the bathroom, housed in a brick cylinder.

The expansive estate, in 47 acres, has 13 Modernist structures in all, like the Brick House (1949-50), where guests would stay.

Johnson would visit the estate with his lifelong partner, art critic David Whitney, who plotted the landscaping and collected much of the art on show.

Tours depart from the Visitor Center in New Canaan, with a basic 1-hour visit to the Glass House, or an extended 2.5-hour tour of the estate on weekends.

12. Devil’s Den Preserve

The largest and most visited nature preserve in Fairfield County is a stone’s throw from Wilton.

You could easily pass half a day on the trails in these 1,756 acres and feel like there’s still much more to see.

More than 500 types of trees and wildflowers, and over 140 bird species have been counted in the Devil’s Den.

The 20 miles of trails will usher you to marvellous features like the panoramic Great Ledge, the ravine and rocky cascade at Ambler Gorge, the marshland of the Saugatuck Wildlife Refuge and the haunting Godfrey Pond, which was dammed for a mill in the 1700s.

13. Wilton River Park Shopping Center

To the south of the town library, this outdoor shopping center has an agreeable, old-time design, with a fine mix of mostly local shops, eateries and a branch of Bow Tie Cinemas.

One store that definitely deserves a closer look, is Goldenberry Gourmet & Gift, stocking hard-to-find specialty treats from all over Europe and the British Isles.

Wilton River Park is also a top-notch dining destination, for Mexican (Cactus Rose Cantina), pan-Asian (Happy Wok), Italian (Tom E Toes Restaurant & Pizza) and casual new American (Craft 14 Kitchen + Bar).

14. Wilton Playshop

There are normally four productions a year at this volunteer-run, not-for-profit community theater.

The Wilton Playshop has a storied history, beginning as long ago as 1937, and provides entertainment for the town and an educational experience for those involved on and off stage.

Some recent shows have included Philadelphia Story, Evita, Chicago, West Side Story and The Lion in Winter.

Separate to each season is the Applause Series, presenting live music, readings, works in progress and more.

At intermission you can repair to the Green Room for refreshments and to meet the members of the cast and production team.

15. Ambler Farm

This 200-year-old farm is owned by the Town of Wilton, and holds educational programs and events all year round and for all ages.

These might be bee-keeping, sheep shearing, maple syruping, cooking classes and gardening workshops.

A landmark on the calendar is the Ambler Farm Day, a fall festival in late-September.

On this day there’s a pumpkin patch, farm animals to meet, an apple slingshot, a pumpkin-firing trebuchet, hayrides and a make-your-own-scarecrow activity.

On Saturdays, June through October, you can come by the farm stand for a changing assortment of fresh produce, like lettuce, basil arugula, kale, fennel, cucumbers, carrots, sweet onions, baby leaks and summer squash, as well as the Ambler’s prized maple syrup.