The Rockwell-esque small town of Weston is right in the middle of Connecticut’s upmarket Fairfield County.
What will strike you right away is the total absence of modern commercial development in a town that has fought hard down the years to preserve its homey character and abundant open space.
The Devil’s Den Preserve covers most of the north of Weston and was founded by the philanthropist daughter of Lucius Pond Ordway, who part-owned the mining company that would become 3M.
After an industrial boom in the early 19th century Weston, went into decline until the 1900s and the roads brought New York commuters, artists, musicians and people from theater world.
In the 21st century Weston is touted one of the best places to live in Connecticut, and among the wealthiest communities in the United States.
Let’s explore the best things to do in and around Weston:
1. Devil’s Den Preserve
Mostly in Weston but also crossing the town line into Redding is the largest nature preserve in Fairfield County and one of the largest in the entire Metropolitan New York area.
Devil’s Den has extraordinary natural diversity on the watershed of the west branch of the Saugatuck River and can be discovered on more than 20 miles of trails, bringing you to waterfalls and high rocky ledges, which we’ll detail below.
Some 140 bird species have been recorded on this land, from pileated woodpeckers to ruffed grouses, and more than 500 kinds of trees and wildflowers grow here.
The main parking area at the end of Pent Road has maps, so you won’t necessarily need to plan your hike in advance.
2. Coley Homestead
The home of the Weston Historical Society is this 19th-century homestead, established in 1834 by David Dimon Coley and occupied by five generations of the Coley family over almost 170 years.
The property, presented as a museum, is made up of the farmhouse (c.1841), a cattle shed (c.1880), a carriage house (c.1840), a big barn and an array of smaller outbuildings.
The farmhouse blends Greek Revival and Victorian elements, having been altered as the century progressed.
In the barn is a large assemblage of Coley-family carpentry tools and farming implements donated to the society by local families.
You’ll seed drills, chisels, saws, planes, skimmers for maple sugaring, pulleys, baskets and anvils going back hundreds of years.
Check the calendar for seasonal events like the Music at the Barn concert series in summer and the Scar Fair every Halloween.
3. Weir Farm National Historic Site
One of only two sites in the national park service to be tied to the visual arts is practically on Weston’s doorstep at Weir Farm.
This was the home of the American Impressionist J. Alden Weir, who welcomed luminaries like John Singer Sargent, Childe Hassam, Albert Pinkham Ryder and John Twachtman here in the early 20th century.
Walden’s house, two separate studios and host of other outbuildings are in 60 acres of bucolic fields and woods, with the idyllic Weir Pond a short walk away.
The property was described by Weir as the “Great Good Place”, and you can tour the art-rich house and studios, learning about Weir, his daughter Dorothy and her sculptor husband Mahonri Young.
The couple took over the property after J. Alden Weir passed away in 1919. May through October the visitor center provides free-to-use art supplies, so you can channel all this inspiration into a masterpiece of your own.
4. Lachat Town Farm
Just over 20 years ago one Leon Lachat deeded his working farm in 42 acres to the town of Weston and the Nature Conservancy as a way of preserving some local agricultural heritage.
The conservancy looks after the wooded area backing onto Devil’s Den, while the town is responsible for the meadow to the front.
The farmhouse, raised in 1770, had been in danger of being torn down, but is going through a long-term restoration thanks to fundraising efforts.
As for things to do, there’s a whole menu of programs at the farm, like knitting classes, storytimes, tai chi, gardening talks, art exhibitions, painting workshops and a farmers’ market on the last Sunday of the month, June through October.
There are also fun seasonal events here, involving bonfires, live music, arts and crafts, face-painting, pony rides and petting zoos.
Come winter, Weston families flock to the farm as it is maybe the best place in town to go sledding.
5. Trout Brook Valley Preserve
Owned by the Aspetuck Land Trust, safeguarding land in Weston, Westport, Fairfield and Easton, the Trout Brook Valley Preserve is a 730-acre tract of land that was saved from developers in 1999. One of people responsible for this achievement was Westport resident and Hollywood star Paul Newman.
Where there was going to be a golf course and luxury condominiums is now pristine nature with scenic vantage points and old apple and blueberry orchards.
You can explore the preserve on 14 miles of trails, some of which link with the adjoining Crow Hill and Jump Hill preserves, and the west shore of the Saugatuck Reservoir, letting you walk for hours without seeing civilization.
6. Norfield Congregational Church
In Weston Center, this dignified Greek Revival church went up in 1830, and has a congregation that goes back to 1757. With a wood frame on a granite foundation, the building has come through plenty of changes in the last 200 years, most notably to the spire, rebuilt in 1987. Now this landmark could be considered Georgian Revival for its round-arched windows and unusually large modillions on the pediments and cornices.
The church, in a complex that includes a parish hall, Christian Education Building, memorial garden and lawn, is the cornerstone of an 18-acre historic district made up of 16 contributing buildings.
The most remarkable of these is the house at 47 Norfield Road, once attached to the Weston Boarding School, and largely unaltered since 1795. In June church lawn is the setting for a country fair that has been running for more than 110 years.
7. Katharine Ordway Preserve
The founder of the Devil’s Den Preserve lived at 177 Good Hill Road in the south of Weston.
Katharine Ordway (1899-1979) is an interesting figure whose father acquired 60% of the stock of the mining company that would later be known as 3M! She made an invaluable contribution to The Nature Conservancy in Connecticut, and after she passed away a piece of her private estate was turned into a 62-acre preserve.
There are three miles of trails in mixed hardwood forest, and the arboretum has a darn redwood and an American chestnut that Ordway personally selected.
Katharine’s mansion is at 177 Good Hill Road, and occasionally opens for tours given by the Weston Historical Society.
8. Amber Falls
From Devil’s Den’s main parking lot on Pent Road you can head off on a 90-minute hike (there and back) to a waterfall deep in west side of the preserve.
Amber Falls is served by a combination of the Pent, McDougal West, Sap Brook and Den Trails.
After crossing a bridge, this small but picturesque falls and their gorge will soon hove into view upstream.
Here a western branch of the Saugatuck River drops around six meters over a flight of cascades, all enclosed in hardwood forest.
9. Great Ledge
At the northern tip of the Devil’s Den preserve is a space by the Saugatuck Reservoir, owned by the Redding Land Trust.
True to its name, Great Ledge consists of a soaring granite gneiss cliff formed in the Ordovician period as long as 500 million years ago.
Great Ledge is frequented by climbers, but there’s a surprisingly light 4.4-mile loop to this spectacular lookout, fitted with information boards telling you about the plants and animal life in the area.
There’s a parking lot on Dayton Road in Redding where you can pick up the Pinchbeck Trail to start this hike.
10. Bisceglie-Scribner Park
Tucked into the woods off the Newtown Turnpike in Weston is a place for residents to get some exercise and take part in sports.
Bisceglie-Scribner Park is just over 50 acres and contains baseball fields, a fitness trail, a picnic area, children’s playground and an inviting swimming pond.
This watched by lifeguards seven days a week, coinciding with the school summer break.
Unfortunately for visitors the pond is open only to Weston residents and their guests.
11. Bradley Edge Tool Company Historic District
If you find yourself on Lyons Plain Road in the east of Weston you’ll be passing through a historical district mostly made up of houses constructed between 1820 and 1925. Nearly all of these have a connection to the Bradley Edge Tool Company, which had a factory complex on the Saugatuck River, lost to fire in 1911.
The outstanding properties here include the 1830s Greek Revival Gershom W. Bradley House(No. 115), Curtis Wood House (No .135) and the stunning Italianate Miles Bradley House, from 1859 sitting at No. 110. There are also fascinating examples of rural workers’ housing in the district, to give you a clear picture of a 19th-century western Connecticut residential community.
12. Ambler Farm
A mile or so over Weston’s town line, Ambler Farm dates back more than 200 years and is owned by the neighboring town of Wilton.
If you’re just dropping by you can wander the organic gardens, cast your eye over the historic buildings, meet the barnyard animals, take a picnic and see what’s on ripe at the seasonal farm stand.
Ambler Farm’s calendar is chock full of educational programs and events, from live music to cooking classes, maple syruping and tomato tasting, some of which require advanced registration and a fee and others that you can attend for free on the spur of the moment.
13. Weston Farmers’ Market
On Saturday mornings, May through mid-October, a farmers’ market pops up on the Coley Homestead shaded lawn.
On a typical visit you can expect to find local produce, honey, homemade sauces, jelly and all kinds of baked goods.
You’ll also come across handmade crafts, soaps, fabrics, and there’s normally plenty of entertainment for families.
As well as the satisfaction of supporting local businesses, you might be pleased to know that vendor rental fees go towards charitable organizations in Weston.
14. Wilton Playshop
You don’t have to travel further than Wilton for an evening of live entertainment, by a theatre group founded more than 80 years ago.
Shows take place in a former church annex, constructed in 1871 and later moved down the hill and joined to what used to be a goat barn.
Wilton Playshop’s plays and musicals are produced with lots of dedication and no little talent.
These are also intimate performances, to the point where you can join the cast in the green room (the former goat barn) during intermission.
Picks from the 2019-20 season included The Lion in Winter, Evita and Jekyll & Hyde.
15. Saugatuck Reservoir
This sizeable body of water warrants a mention as it makes up the entirety of Weston’s north-east boundary.
Impounding the river of the same name, the Saugatuck Reservoir provides water for the city of Norwalk and covers more than 800 acres.
It was dammed in the 1930s, but only after a lot of wrangling, as many residents refused to sell their property.
After the association created to fight the reservoir had been defeated by the courts and Bridgeport Hydraulic Company Holdings, the villages of Hull and Valley Forge were submerged beneath these waters.
The current owner is Aquarion, which sells season fishing permits ($25) if you have a Connecticut fishing licence.
Among the many species recorded in the reservoir are small and largemouth bass, sunfish, yellow and white perch and brook, brown and rainbow trout.
For walkers, the Saugatuck Valley Trail weaves through Aquarion land from the northern tip down the west shore.