Top 15 Attractions and Activities in Weston, Connecticut

The picturesque small town of Weston is located in the heart of Connecticut’s affluent Fairfield County.

You will immediately notice the complete lack of modern commercial development in a town that has diligently worked over the years to maintain its quaint character and plentiful open space.

The Devil’s Den Preserve encompasses much of the northern region of Weston and was established by the philanthropic daughter of Lucius Pond Ordway, a part-owner of the mining company that evolved into 3M.

After experiencing an industrial boom in the early 19th century, Weston went into decline until the early 1900s, when the roads attracted New York commuters, artists, musicians, and individuals from the theater world.

In the contemporary era, Weston is recognized as one of the premier residential areas in Connecticut and ranks among the wealthiest communities in the United States.

Let’s delve into the prime activities available in and around Weston:

1. Devil’s Den Preserve

Primarily located in Weston but also extending into Redding, this is the largest nature preserve in Fairfield County and one of the largest in the entire Metropolitan New York area.

Devil’s Den features remarkable natural diversity within the watershed of the west branch of the Saugatuck River, which can be explored via more than 20 miles of trails, guiding you to waterfalls and elevated rocky overlooks, detailed further below.

Approximately 140 bird species have been observed within this preserve, ranging from pileated woodpeckers to ruffed grouses, alongside over 500 varieties of trees and wildflowers.

The primary parking area, located at the end of Pent Road, provides maps, allowing you to embark on your hike without needing to meticulously plan ahead.

2. Coley Homestead

This 19th-century homestead, established in 1834 by David Dimon Coley, is the home of the Weston Historical Society and has been occupied by five generations of the Coley family over nearly 170 years.

The estate, now presented as a museum, comprises the farmhouse (c.1841), a cattle shed (c.1880), a carriage house (c.1840), a substantial barn, and a variety of smaller outbuildings.

The farmhouse exquisitely blends Greek Revival and Victorian architectural styles, having undergone modifications as the century progressed.

Within the barn, visitors can find a substantial collection of Coley-family carpentry tools and farming implements, donated to the society by local residents.

You’ll discover seed drills, chisels, saws, planes, maple sugaring skimmers, pulleys, baskets, and anvils with origins spanning hundreds of years.

Consult the calendar for seasonal events, such as the Music at the Barn concert series during summer and the Scar Fair held every Halloween.

3. Weir Farm National Historic Site

Only one of two sites within the national park service directly associated with the visual arts, Weir Farm is virtually at Weston’s doorstep.

This was the residence of American Impressionist J. Alden Weir, who hosted renowned artists such as John Singer Sargent, Childe Hassam, Albert Pinkham Ryder, and John Twachtman during the early 20th century.

The property includes Walden’s house, two separate studios, and numerous other outbuildings within 60 acres of picturesque fields and forests, with Weir Pond situated a short distance away.

Weir described this property as the “Great Good Place,” and visitors can tour the art-filled house and studios, gaining insight into Weir, his daughter Dorothy, and her sculptor husband Mahonri Young.

The couple managed the property following J. Alden Weir’s passing in 1919. From May through October, the visitor center offers complimentary art supplies, allowing you to transform your inspiration into a creative masterpiece.

4. Lachat Town Farm

Over two decades ago, Leon Lachat transferred his working farm, encompassing 42 acres, to the town of Weston and the Nature Conservancy to help protect some of the local agricultural heritage.

The conservancy manages the wooded area adjacent to Devil’s Den, while the town oversees the meadow at the front of the property.

The farmhouse, constructed in 1770, was at risk of demolition but is currently undergoing a long-term restoration, aided by fundraising initiatives.

A variety of programs are available at the farm, including knitting classes, storytelling sessions, tai chi, gardening discussions, art exhibitions, painting workshops, and a farmers’ market on the last Sunday of each month from June through October.

Additionally, there are enjoyable seasonal activities featuring bonfires, live music, arts and crafts, face painting, pony rides, and petting zoos.

During winter, Weston families frequently visit the farm, as it is regarded as one of the premier locations in town for sledding.

5. Trout Brook Valley Preserve

Protected by the Aspetuck Land Trust, which conserves land in Weston, Westport, Fairfield, and Easton, the Trout Brook Valley Preserve encompasses 730 acres of land that was preserved from developers in 1999. Westport resident and Hollywood actor Paul Newman played a significant role in this preservation effort.

Formerly designated for a golf course and luxury condominiums, this area is now a pristine natural environment featuring scenic viewpoints and historic apple and blueberry orchards.

Visitors can traverse the preserve on 14 miles of trails, some of which connect with the adjoining Crow Hill and Jump Hill preserves, as well as the western shore of the Saugatuck Reservoir, providing the opportunity to walk for hours without encountering signs of civilization.

6. Norfield Congregational Church

Located in Weston Center, this elegant Greek Revival church was erected in 1830 and has a congregation that dates back to 1757. With a wooden frame on a granite foundation, the structure has undergone numerous changes in the last 200 years, particularly to its spire, which was rebuilt in 1987. This landmark could now be described as Georgian Revival due to its round-arched windows and unusually large modillions on the pediments and cornices.

The church complex features a parish hall, a Christian Education Building, a memorial garden, and a lawn, forming the cornerstone of an 18-acre historic district containing 16 contributing buildings.

The most notable of these is a residence at 47 Norfield Road, once connected to the Weston Boarding School, and largely remains unaltered since 1795. Each June, the church lawn hosts a country fair that has been celebrated for over 110 years.

7. Katharine Ordway Preserve

The benefactor of the Devil’s Den Preserve resided at 177 Good Hill Road in southern Weston.

Katharine Ordway (1899-1979) is a notable figure whose father acquired 60% of the shares of the mining firm that later became 3M. She made significant contributions to The Nature Conservancy in Connecticut, and upon her passing, a portion of her estate was transformed into a 62-acre preserve.

The preserve features three miles of trails set within a mixed hardwood forest, and the arboretum includes a rare redwood tree and an American chestnut personally chosen by Ordway.

Katharine’s mansion at 177 Good Hill Road occasionally opens for guided tours conducted by the Weston Historical Society.

8. Amber Falls

From the main parking lot at Devil’s Den on Pent Road, visitors can embark on a 90-minute round-trip hike to reach a waterfall nestled deep within the western side of the preserve.

Amber Falls can be accessed through a combination of the Pent, McDougal West, Sap Brook, and Den Trails.

After traversing a bridge, this small yet striking waterfall and its gorge will soon appear in view upstream.

Here, the western branch of the Saugatuck River cascades approximately six meters over a series of drops, all surrounded by hardwood forest.

9. Great Ledge

Located at the northern end of the Devil’s Den Preserve is a region by the Saugatuck Reservoir, owned by the Redding Land Trust.

True to its moniker, Great Ledge features an impressive granite gneiss cliff that was formed during the Ordovician period, approximately 500 million years ago.

This area is popular among climbers; however, there is also a surprisingly gentle 4.4-mile loop trail leading to this stunning lookout, equipped with informational boards that provide insights about the local flora and fauna.

A parking lot on Dayton Road in Redding allows access to the Pinchbeck Trail to commence this hike.

10. Bisceglie-Scribner Park

Tucked away in the woods off the Newtown Turnpike in Weston lies a space for residents to engage in physical activities and enjoy sports.

Bisceglie-Scribner Park spans just over 50 acres and features baseball fields, a fitness trail, a picnic area, a children’s playground, and a welcoming swimming pond.

This pond is supervised by lifeguards seven days a week during the school summer break.

Unfortunately, access to the pond is restricted to Weston residents and their invited guests.

11. Bradley Edge Tool Company Historic District

Should you find yourself along Lyons Plain Road in eastern Weston, you will traverse a historic district primarily characterized by residences constructed between 1820 and 1925. Almost all of these properties are related to the Bradley Edge Tool Company, whose factory complex along the Saugatuck River was devastated by fire in 1911.

Noteworthy properties in this area include the Greek Revival Gershom W. Bradley House (No. 115), Curtis Wood House (No. 135), and the striking Italianate Miles Bradley House from 1859, located at No. 110. Additionally, the district contains fascinating examples of rural workers’ housing, providing insight into 19th-century western Connecticut residential communities.

12. Ambler Farm

Located just over a mile away from Weston’s town line, Ambler Farm boasts a history of more than 200 years and is owned by the adjacent town of Wilton.

If you’re merely visiting, you can stroll through the organic gardens, view the historic structures, interact with barnyard animals, enjoy a picnic, and explore what is in season at the farm’s seasonal stand.

Ambler Farm’s schedule is filled with educational programs and events, ranging from live music to cooking classes, maple syrup harvesting, and tomato tastings. Some activities require advanced registration and fees, while others can be attended spontaneously at no cost.

13. Weston Farmers’ Market

On Saturday mornings from May through mid-October, a farmers’ market takes place on the shaded lawn of the Coley Homestead.

During a typical visit, attendees can expect to find local produce, honey, homemade sauces, preserves, and a variety of baked items.

Additionally, handmade crafts, soaps, textiles, and ample family-friendly entertainment are usually available.

Alongside the satisfaction of supporting local businesses, vendors’ rental fees are allocated to charitable organizations within Weston.

14. Wilton Playshop

No need to venture further than Wilton for an evening filled with live entertainment, thanks to a theater group that has been operating for over 80 years.

Performances occur in a repurposed church annex, originally constructed in 1871 and later relocated and connected to what was previously a goat barn.

Producing plays and musicals, Wilton Playshop showcases dedication and considerable talent.

These productions are intimate, to the extent that audiences can join the cast in the green room (the former goat barn) during intermission.

Selections from the 2019-20 season included The Lion in Winter, Evita, and Jekyll & Hyde.

15. Saugatuck Reservoir

This substantial body of water is noteworthy as it forms the entirety of Weston’s northeastern boundary.

Impounding the river of the same name, the Saugatuck Reservoir supplies water to the city of Norwalk and spans over 800 acres.

Although it was dammed in the 1930s, this development encountered considerable opposition, as many residents were reluctant to sell their properties.

After the association formed to contest the reservoir’s construction was defeated in court by the Bridgeport Hydraulic Company Holdings, the villages of Hull and Valley Forge were submerged beneath its waters.

The current proprietor is Aquarion, which offers seasonal fishing permits ($25) to individuals possessing a Connecticut fishing license.

The reservoir is home to numerous fish species, including small and largemouth bass, sunfish, yellow and white perch, as well as brook, brown, and rainbow trout.

For those who enjoy hiking, the Saugatuck Valley Trail meanders through Aquarion’s land, stretching from the northern point down the western shore.