15 Best Things to Do in Winchester (MA)

Written by Jan Meeuwesen
Updated on
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Embedded in a valley below the eastern shoulder of the Middlesex Fells, Winchester is a wealthy suburban town with a gorgeous Victorian commercial district.

Winchester Center is bounded by old millponds along the Aberjona River, and has a rich assortment of Historicist architecture.

For outdoor recreation, all you have to do is walk east from downtown Winchester, and in five minutes you’ll be on the granite slopes of the Middlesex Fells Reservation.

Elsewhere there’s a preserved 19th-century farm, beachfront on the Mystic Lakes and a highly regarded photography museum.

Winchester Center has also recently been hooked up to the Tri-Community Greenway, circumventing those hills along an old railroad spur and connecting with Stoneham.

1. Winchester Center

Winchester Center Aerial ViewSource: Wangkun Jia / shutterstock
Winchester Center Aerial View

Woven with a series of ponds, Winchester has an exquisite downtown area, where several major arteries meet at a roundabout.

This district was developed in two flurries of construction following the arrival of the Boston and Lowell Railroad in 1835 and then after the end of the Civil War, creating a showcase of Victorian architecture.

One dominant style is Romanesque Revival, which can be seen at the beautiful Town Hall (1887), Winchester Savings Bank (1892) and the arresting Brown and Stanton Block (1879), on the roundabout at the corner of Main Street and Mount Vernon Street.

There’s a clutch of restaurants and coffee houses, all close to each other by the roundabout, with a summer farmers’ market on the common and outdoor exhibits throughout the district via the Griffin Museum of Photography.

2. Middlesex Fells Reservation

Middlesex Fells ReservationSource: Jonathan Welch / shutterstock
Middlesex Fells Reservation

Heading up the slope to the east, you can set off on foot from Winchester Center and soon find yourself in this 2,200 acre tract of rugged wooded hills and lakes, crisscrossed by more than 100 miles of trails.

The Middlesex Fells Reservation is vital for Winchester’s water supply, with the active North, Middle and South Reservoirs, all on the west side of the recreation area.

Approaching from this side, you can easily get onto the eight-mile Skyline Trail, for astonishing vistas of downtown Boston, or you can admire those secluded lakes via the challenging Reservoir Trail.

On the east side of I-93 is Spot Pond where you can rent canoes and kayaks in summer, and visit Stone Zoo, famed for its delightful light display in the holiday season.

3. Griffin Museum of Photography

Griffin Museum of PhotographySource: Daderot / Wikimedia | CC0
Griffin Museum of Photography

In a cute Colonial-style complex next to Judkins Pond, the Griffin Museum of Photography was founded in 1992 by noted photographer Arthur Griffin (1903-2001).

A pioneer of color photography, Griffin worked as a photojournalist for the Boston Globe, Life, and Time and published several books.

When it opened, the Griffin Museum became the first museum in the Boston area to be dedicated to photography, and is a highly-regarded institution with a number of satellite galleries.

There’s a bustling program of shows at the museum’s own Main Gallery, Griffin Gallery and Griffin Atelier Gallery, featuring the work of leading contemporary photographers.

4. Wright-Locke Farm

Wright-Locke FarmSource: Massachusetts Office of Travel & Tourism / Flickr | CC BY-ND
Wright-Locke Farm

In 2007, to stop a large-scale housing development, the Town of Winchester purchased this historic farm, which was then sold to the Wright-Locke Land Trust in 2015.

In the late 18th century, the land that became the Wright-Locke Farm was owned by the famous explorer Philemon Wright (1760-1839), who sold it to Josiah Locke in 1800.

Locke and his descendants developed the farm, and it remained in the family into the 20th century. There’s an elegant Greek Revival house, built around 1828, and a working community farm with trails, goats, PYO raspberry patches and a lovely farm stand.

The Wright-Locke Farm is a hub for activities all year, from outdoor concerts to children’s camps and a diversity of workshops.

5. Tri-Community Greenway

Tri-Community GreenwaySource: John Phelan / Wikimedia | CC BY-SA 4.0
Tri-Community Greenway

A total success since officially opening in 2019, the Tri-Community Greenway links Winchester Center with Stoneham’s Central Square.

The trail is almost seven miles long, with much of its northern section along the right-of-way of the Stoneham Branch (1863) of the Boston & Lowell Railroad.

This is a hassle-free link between two thriving downtown districts, perfect for commuters who don’t want to use a car.

The Tri-Community Greenway also stands as an excellent leisure amenity, with a spur to Horn Pond, close by in Woburn, and a large green buffer, 45 feet wide along the old rail corridor.

In Winchester the trail traces the Aberjona River, Mill Pond and Judkins Pond, passing through Ginn Field Park and terminating at Wedgemere station.

6. Shannon Beach

BeachSource: LOGVINYUK YULIIA / shutterstock

There’s a freshwater beach a few steps from Wedgemere station in Winchester, on a little peninsula at Upper Mystic Lake.

Part of Mystic Lakes State Park (more below), Shannon Beach is open from Memorial Day weekend, and when we wrote this article had recently upgraded its facilities, adding a brand new bathhouse and new benches and picnic tables.

The beach itself is surprisingly large, and is edged by ample grassy and wooded space for barbecues and games, with an enormous playground for children.

7. Mystic Lakes State Park

Mystic Lakes State ParkSource: Micha Weber / shutterstock
Mystic Lakes State Park

Shannon Beach is one element of a pair of lakes in the south of Winchester, at the head of the Mystic River. This encompasses the Upper and Lower Mystic Lakes, which are a go-to for recreation, on the water and along their verdant banks.

The upper lake is the home of Medford Boat Club and the sailing pavilion for Tufts University. On a more casual basis, Paddle Boston has a location by the dam in summer, for canoe and kayak rentals.

The Mystic Lakes State Park is the uppermost of four reservations along the Mystic River, the banks of which are almost completely accessible to the public.

Linking with the Tri-Community Greenway in Winchester, you can walk or ride by the river and its tributaries on 25 miles of trails that are gradually becoming interconnected as part of the Mystic Greenways project.

8. Sanborn House

Sanborn HouseSource: User:Magicpiano / Wikimedia | CC BY-SA 4.0
Sanborn House

One of the finest pieces of residential architecture in Winchester is a rare surviving country house, built in the Beaux-Arts style in 1906.

This was the home of Oren Sanborn, son of James Sanborn, who co-founded the Chase & Sanborn Coffee Company.

One reason for Sanborn House’s survival is that the estate was sold off in 1920 to the Religious of Christian Education, who established a grade school here.

This eventually became Ambrose Elementary School, which moved into a new adjacent building in 2003, and since that time the Winchester Historical Society has conducted a long-term restoration of Sanborn House.

You can come to see the interior on Tuesdays, Wednesdays and Thursdays, while in winter the lawn is a favorite sledding hill for local children.

9. Horn Pond Recreation Area

Horn PondSource: Chantel Dopp / shutterstock
Horn Pond

The destination for that spur of the Tri-Community Greenway is a 102-acre pond, fringed by wooded parkland on the south and west sides.

You can walk or jog around the entirety of Horn Pond on a paved trail, and it’s worth taking a seat along Arlington Rd down the east side to watch the sun go down over the water.

Summer is a fine time to visit the pond, when Boating in Boston is on hand, renting out kayaks (single or double) by the hour. If you have your own non-motorized vessel there are boat launches on the south and north shores.

10. Horn Pond Mountain (Mt. Towanda)

Horn Pond MountainSource: Kristin "Shoe" Shoemaker / Flickr | CC BY-ND
Horn Pond Mountain

Looming over the south side of Horn Pond there’s a tall hill, still in Woburn but surrounded on three sides by Winchester land.

In the middle of the 20th century the steep slopes of Horn Pond Mountain were home to a ski resort, and faint remnants of the chair lifts can still be seen amid the vegetation.

If you have about 45 minutes to spare, you can take a looping trail from the south shore of the pond up to the summit, and on the southeast side is another place where you can take in the Boston skyline.

11. Winchester Farmers’ Market

Farmers MarketSource: Matej Kastelic / shutterstock
Farmers Market

Every Saturday morning through the end of October there’s a farmer’s market on the Town Common.

When we wrote this article, the market had about ten permanent vendors, and twice as many part-time vendors, with weekly updates provided by the organizers on facebook.

You can shop for fruit and vegetables for local farms including Wright-Locke Farm, as well as sustainable seafood, pasture-raised meats, maple syrup, eggs, tea mixes, breads, cookies, pies, bagels, pastries and artisanal candies.

There’s often a range of enticing prepared food, from stews to flatbreads, Chinese dumplings and Congolese specialties.

12. The Brooks Estate

Brooks EstateSource: Robert Gray - Newton, MA / Flickr | CC BY
Brooks Estate

In 1880, Shepherd Brooks (1837-1922), a member of a prominent Medford family, commissioned the Peabody & Stearns firm to build him an opulent Queen Anne mansion, on an estate more than 80 acres in size.

Today the Brooks Estate is owned by the town, and while there are long-term plans to restore the manor house, you’re free to explore the property.

Backdropped by that fine Victorian architecture, this has wetlands, a pond, mature stands of maple and oak, with trails that connect with Winchester’s Brooks-Parkhurst Town Forest for an extended walk in the woods.

13. Whipple Hill

Whipple HillSource: Daderot / Wikimedia | CC0
Whipple Hill

The trails on Wright-Locke Farm cross over into this 120-acre conservation area belonging to Lexington.

The summit of Whipple Hill is the highest point in the town, at 375 feet, and the enclosing property has mature hardwood and pine forest, rocky ledges, wetlands and the lush banks of Whipple Brook.

That peak is at the north end, and can be accessed on the red-blazed Geology Loop, while there’s also a Farm/Wetland Loop linking with Wright-Locke Farm, a Conservation Trail and a section of Lexington’s ACROSS trail system.

14. Winter Pond

Winter Pond, WinchesterSource: Friends of Winter Pond / Facebook
Winter Pond

One of Winchester’s larger bodies of water is easy to miss, at the foot of Horn Pond Mountain on the west side of the town.

Winter Pond is geologically significant as a kettle hole pond, created by glacial activity at the end of the last Ice Age.

Woodside Road divides the pond into larger (west) and smaller (sections), and there’s a makeshift parking area along the road.

There’s a kiosk and a bench so you can linger for a while to savor one of the prettiest scenes in the town, and another lovely place to be at sunset.

15. Photoville Fence

Winchester Photoville FenceSource: Griffin Museum of Photography / Facebook
Winchester Photoville Fence

Now an annual tradition, this summer pop-up exhibition is a partnership between the Griffin Museum, Photoville and the Winchester Cultural District.

Normally opening in June, the Photoville Fence is set up mostly on the shores of Judkins Pond next to the museum building.

Here you’ll encounter a series of photo installations, featuring the work of regional, national and international contemporary photographers.

Recent iterations have been produced in collaboration with a range of institutions, businesses and publications, including the United Nations, Leica Camera USA and Atlantic Magazine.


15 Best Things to Do in Winchester (MA):

  • Winchester Center
  • Middlesex Fells Reservation
  • Griffin Museum of Photography
  • Wright-Locke Farm
  • Tri-Community Greenway
  • Shannon Beach
  • Mystic Lakes State Park
  • Sanborn House
  • Horn Pond Recreation Area
  • Horn Pond Mountain (Mt. Towanda)
  • Winchester Farmers’ Market
  • The Brooks Estate
  • Whipple Hill
  • Winter Pond
  • Photoville Fence