15 Things to Do in Weston (CT)

The Rockwell-esque town of Weston is in the heart of Connecticut’s upscale Fairfield County.

You’ll be immediately struck by the complete absence of modern commercial development in a town that has struggled for years to maintain its welcoming character and abundance of open spaces.

Devil’s Den Preserve covers much of North Weston and was founded by Lucius Pond Ordway’s philanthropist daughter, who partly owns the mining company that would become 3M.

After Weston’s industrial boom in the early 1800s, which didn’t begin to decline until the 1900s, the road brought New York’s commuters, artists, musicians, and theatergoers.

In the 21st century, Weston is known as one of the best places to live in Connecticut and one of the wealthiest communities in the United States.

Let’s explore the best things to do in and around Weston:

1. Devil’s Lair Sanctuary


Most are in Weston, but also across the town line into Reading is the largest nature reserve in Fairfield County and one of the largest in the entire New York metropolitan area.

Devil’s Lair has remarkable natural diversity in the Saugatuck West Tributary and can be found on more than 20 miles of trails that take you to waterfalls and high rock ledges, which we’ll detail below.

About 140 species of birds have been recorded on this land, from mounds of woodpeckers to grouse, and more than 500 species of trees and wildflowers grow here.

The main car park at the end of Pent Road has a map, so you don’t necessarily need to plan your hike in advance.

2. Kohli Homestead

Kohli Homestead

Home to the Weston Historical Society is this 19th century homestead, established by David Dimon Coley in 1834 and occupied by five generations of the Coley family for nearly 170 years.

Presented as a museum, the property consists of a farmhouse (c.1841), a cowshed (c.1880), a carriage house (c.1840), a large barn and a series of smaller outbuildings.

The farmhouse incorporates elements of the Greek Revival and Victorian eras, changing over the centuries.

The barn houses a large collection of Coley family woodworking and farming tools, donated to the community by local families.

You’ll use planters, chisels, saws, planes, skimmers for maple syrup, pulleys, baskets and anvils dating back hundreds of years.

Check out the calendar for seasonal events like the Barn Concert Series music in summer and the Scar Fair every Halloween.

3. Will Farm National Historic Site

Will Farm National Historic Site

One of only two visual arts-related locations in the National Park Service is actually right on the doorstep of Weir Farm in Weston.

This is the hometown of American Impressionist painter J. Alden Weir, who in the early 1900s hosted such luminaries as John Singer Sargent, Childe Hassam, Albert Pinkham Ryder and John Twachtman.

Walden’s house, two separate studios and many other outbuildings are set in 60 acres of bucolic landscape and woods, just a short walk from idyllic Weir Pond.

Described by Weir as a ‘nice place’, you can visit the art-rich house and studio to learn about Weir, his daughter Dorothy and her sculptor husband Mahonri Young.

The couple took over the property after J. Alden Weir’s death in 1919. From May to October, the visitor center offers free-to-use art supplies, so you can turn all these inspirations into your own masterpiece.

4. Racha Town Farm

Racha Town Farm

Just over 20 years ago, a Leon Lachat transferred his 42-acre working farm to the Town of Weston and The Nature Conservancy as a way to preserve the local agricultural heritage.

The sanctuary manages the wooded area backed by the devil’s lair, while the town takes care of the meadows ahead.

The farmhouse, built in 1770, was in danger of being demolished, but is undergoing a long-term restoration thanks to a fundraising campaign.

As for things to do, the farm has a full menu of items such as weaving classes, story time, tai chi, gardening talks, art exhibitions, painting workshops and a farmers market on the last Sunday of each month, June to October.

There are also fun seasonal activities here, including campfires, live music, arts and crafts, face painting, pony rides and a petting zoo.

Winter is here and Weston’s family flocks to the farm because it’s probably the best sledding spot in town.

5. Trout Valley Reserve

Trout Valley Reserve

Owned by the Aspetuck Land Trust, which protects lands in Weston, Westport, Fairfield and Easton, Trout Brook Valley Preserve is a 730-acre property rescued from developers in 1999. One of those responsible for this achievement is Westport resident and Hollywood star Paul Newman.

What used to be a golf course and luxury apartments is now pristine nature, with scenic vantage points and ancient apple and blueberry orchards.

You can explore the reserve on 14 miles of trails, some of which connect to the adjoining Crow Hill and Jump Hill Reserves and the west shore of the Saugatuck Reservoir, allowing you to walk for hours without seeing civilization.

6. Norfield Congregational Church

Norfield Congregational Church

In the heart of Weston, this stately Greek Revival church was built in 1830 with a congregation dating back to 1757. With a wooden frame on a granite foundation, the building has undergone many changes over the past 200 years, most notably the spire, which was rebuilt in 1987. Now the landmark can be considered a Georgian Revival because of its round arched windows and unusually large ornamentation on the gables and cornices.

Located in a complex that includes the Parish Hall, Christian Education Building, Memorial Gardens, and Lawn, the church is the cornerstone of an 18-acre historic district comprised of 16 contributing buildings.

Most notable of these is the house at 47 Norfield Road, which once belonged to Weston Boarding School and has remained largely unchanged since 1795. June Church Lawn is the site of a country fair for over 110 years.

7. Katherine Oldway Reserve

Katherine Oldway Reserve

The founders of Devil’s Den Reserve live at 177 Goodhill Road, South Weston.

Katharine Ordway (1899-1979) was an interesting figure whose father bought a 60% stake in what would become known as 3M’s mining company! She made an invaluable contribution to The Nature Conservancy in Connecticut, and after her death, a piece of her private estate was turned into a 62-acre preserve.

There are three miles of trails in the mixed hardwood forest, and the botanical garden has a damn redwood and an Aldway hand-picked American chestnut.

Katherine’s mansion at 177 Goodhill Road is occasionally open for tours by the Weston Historical Society.

8. Amber Falls

Amber Falls

From Devil’s Den main car park on Pent Road, you can hike 90 minutes (round trip) to the waterfall deep on the west side of the reserve.

Amber Falls consists of the Pent, McDougal West, Sap Brook and Den Trails.

After crossing a bridge, the small but picturesque waterfalls and their gorges soon come into view upstream.

Here, a western tributary of the Saugatuck falls about 6 meters from a small waterfall, all surrounded by hardwood forest.

9. Big Ledge

large ledge

At the northern end of the Devil’s Den Reserve is a space next to Saugatuck Reservoir owned by the Reading Land Trust.

True to its name, the Great Ledge consists of a towering granite gneiss cliff formed 500 million years ago during the Ordovician period.

The Great Ledge is frequented by climbers, but this spectacular lookout has a surprisingly light loop of 4.4 miles, complete with information boards telling you about the plant and animal life in the area.

There is a parking lot on Dayton Road in Reading, where you can start this hike with the Pinch Baker trail.

10. Biscelle-Scribner Park


Hidden in the woods by the Weston Newtown Turnpike, it is a place for residents to exercise and play sports.

Bisceglie-Scribner Park spans over 50 acres and includes baseball fields, fitness trails, picnic areas, a children’s playground and a stunning swimming pool.

Lifeguards watch 7 days a week, just in time for the school summer break.

Unfortunately for tourists, the pond is only open to Weston residents and their guests.

11. Bradley Edge Tools Historic District

Bradley Edge Tools Historic District

If you find yourself on Lyon Plain Road east of Weston, you’ll pass a historic district made up mostly of houses built between 1820 and 1925. Almost all of them were related to the Bradley Edge Tool Company, which owned the factory complex on the Saugatuck River, which caught fire in 1911.

Outstanding properties here include the 1830s Greek Revival Gershom W. Bradley House (No. 115), the Curtis Wood House (No. 135) and the stunning Italianate Miles Bradley House, built in 1859 in No. 135 No. 110. Rural worker housing in the area gives you a clear view of the residential communities of western Connecticut in the 19th century.

12. Ambler Farms

Ambler Farm

About a mile from the Weston town line, Ambler Farm dates back more than 200 years and is owned by the neighbouring town of Wilton.

If you’re just passing by, you can stroll through the organic gardens, set your sights on historic buildings, meet barnyard animals, have a picnic, and see the deli at the seasonal farm stand.

Ambler Farm’s calendar is full of educational programs and events, from live music to cooking classes to maple syrup and tomato tastings, some of which require advance registration and payment, while others are free to attend.

13. Weston Farmers Market

Weston Farmers Market

On Saturday mornings from May to mid-October, a farmers market takes place on the shady lawn of the Kohli Homestead.

On a typical visit you will find local produce, honey, homemade sauces, jellies and a variety of baked goods.

You’ll also come across handcrafts, soaps, fabrics, and generally plenty of family-friendly entertainment.

In addition to the satisfaction of supporting local businesses, you may be pleased to learn that vendor rentals go to Weston’s charitable organization.

14. Wilton Game Store


You don’t have to travel farther than Wilton to enjoy live entertainment from a troupe founded more than 80 years ago.

The show takes place in a former church annex, built in 1871 and later moved down the hillside to connect with the former goat barn.

Wilton Playshop’s plays and musicals are produced with a great deal of dedication and talent.

These are also intimate shows, so much so that you can join the cast of The Green Room (former goat shed) at halftime.

Picks for the 2019-20 season include The Lion in Winter, Evita and Jekyll & Hyde.

15. Saugatuck Reservoir

saugatuck res.

This sizable body of water is worth mentioning because it forms the entire northeastern boundary of Weston.

The Saugatuck Reservoir, which fills the river of the same name and supplies the city of Norwalk, covers more than 800 acres.

It was dammed in the 1930s, but after much rowing, many residents refused to sell their property.

The villages of Hull and Valley Forge were submerged under these waters after an association formed to fight the reservoir was defeated by the court and Bridgeport Hydraulics Holdings.

The current owner is Aquarion, which sells seasonal fishing licenses ($25) if you have a Connecticut fishing license.

Many species recorded in the reservoir include small and largemouth bass, sunfish, yellow and white bass and creek, brown trout and rainbow trout.

For walkers, the Saugatuck Valley Trail crosses Aquarion Land from the northern end and runs along the western shore.

Where to Stay: Best Hotels in Weston, CT (CT)
Lowest Price Guarantee