Top 15 Attractions and Activities in Winchester, MA

Embedded in a valley below the eastern shoulder of the Middlesex Fells, Winchester is an affluent suburban town featuring a beautiful Victorian commercial district. Additionally, the town boasts an array of historic architecture that enriches its cultural landscape.

Winchester Center is bordered by historic millponds along the Aberjona River, showcasing a diverse range of Historicist architecture. For outdoor activities, a simple eastward stroll from downtown Winchester will lead you to the granite slopes of the Middlesex Fells Reservation within five minutes.

Moreover, the area includes a well-preserved 19th-century farm, beachfront access at Mystic Lakes, and a highly regarded photography museum. Recently, Winchester Center has been connected to the Tri-Community Greenway, which circumvents the nearby hills along an old railroad spur, establishing a link with Stoneham.

1. Winchester Center

Characterized by a series of serene ponds, Winchester boasts an exquisite downtown area, where several major thoroughfares converge at a roundabout. This district was developed during two significant construction phases, following the arrival of the Boston and Lowell Railroad in 1835, and again after the conclusion of the Civil War, resulting in a showcase of Victorian architecture.

Among the prevalent architectural styles is Romanesque Revival, observable at the majestic Town Hall (1887), Winchester Savings Bank (1892), and the striking Brown and Stanton Block (1879), located at the roundabout at Main Street and Mount Vernon Street. The area features a variety of restaurants and coffee shops concentrated around the roundabout, along with a summer farmers’ market held in the common area and outdoor exhibits available throughout the district, courtesy of the Griffin Museum of Photography.

2. Middlesex Fells Reservation

Ascending the slope to the east, you can embark on foot from Winchester Center and soon find yourself in this expansive 2,200-acre region of rugged wooded hills and lakes, traversed by over 100 miles of trails. The Middlesex Fells Reservation is essential for the town’s water supply, housing the active North, Middle, and South Reservoirs, all situated on the western side of the recreational area.

From this approach, one can easily access the eight-mile Skyline Trail, offering breathtaking views of downtown Boston, or explore the secluded lakes via the challenging Reservoir Trail. On the eastern side of I-93 lies Spot Pond, a site where visitors can rent canoes and kayaks during the summer and also visit Stone Zoo, which is renowned for its enchanting holiday light display.

3. Griffin Museum of Photography

Housed within a charming Colonial-style complex adjacent to Judkins Pond, the Griffin Museum of Photography was founded in 1992 by the esteemed photographer Arthur Griffin (1903-2001). A pioneer in color photography, Griffin served as a photojournalist for prestigious publications such as the Boston Globe, Life, and Time, and authored several notable books.

Upon its inception, the Griffin Museum became the first dedicated photography museum in the Boston area and is recognized as a reputable institution featuring several satellite galleries. The museum hosts an active schedule of exhibitions in its Main Gallery, Griffin Gallery, and Griffin Atelier Gallery, showcasing the works of prominent contemporary photographers.

4. Wright-Locke Farm

In 2007, to prevent a large residential development, the Town of Winchester acquired this historic farm, which was subsequently transferred to the Wright-Locke Land Trust in 2015. In the late 18th century, this parcel of land was owned by the prominent explorer Philemon Wright (1760-1839), who sold it to Josiah Locke in 1800.

Locke and his descendants cultivated the farm, which remained in the family well into the 20th century. The property features an elegant Greek Revival house, built approximately in 1828, as well as a functioning community farm boasting trails, goats, pick-your-own raspberry patches, and a charming farm stand. Wright-Locke Farm serves as a community hub for various activities year-round, including outdoor concerts, children’s camps, and a variety of workshops.

5. Tri-Community Greenway

Since its official opening in 2019, the Tri-Community Greenway has been a resounding success, linking Winchester Center with Stoneham’s Central Square. The trail extends nearly seven miles, largely following the right-of-way of the Stoneham Branch (1863) of the Boston & Lowell Railroad.

This pathway provides a convenient connection between two vibrant downtown districts, ideal for commuters opting not to drive. In addition, the Tri-Community Greenway serves as an exceptional recreational resource, with a spur leading to Horn Pond nearby in Woburn, and a generous 45-foot-wide green buffer alongside the former rail corridor. Within Winchester, the trail meanders along the Aberjona River, Mill Pond, and Judkins Pond, passing through Ginn Field Park and culminating at Wedgemere station.

6. Shannon Beach

Located just steps from Wedgemere station in Winchester, Shannon Beach is situated on a small peninsula at Upper Mystic Lake. As part of Mystic Lakes State Park, Shannon Beach opens its doors on Memorial Day weekend and, as of the time of this article, had recently upgraded its facilities, enhancing the bathhouse and adding new benches and picnic tables.

This expansive beach area is bordered by ample grassy and wooded spaces suitable for barbecues and games, complemented by a large playground for children.

7. Mystic Lakes State Park

Shannon Beach is one aspect of a pair of lakes situated in the southern part of Winchester, at the head of the Mystic River, encompassing the Upper and Lower Mystic Lakes. These lakes serve as popular locations for recreation, both on the water and along their lush banks. The upper lake is home to the Medford Boat Club and Tufts University’s sailing pavilion. In a more casual setting, Paddle Boston offers canoe and kayak rentals at the dam during the summer months.

Mystic Lakes State Park is the northernmost of four reservations found along the Mystic River, with nearly all of its banks being accessible to the public. Connecting with the Tri-Community Greenway in Winchester, visitors can walk or bike along the river and its tributaries on 25 miles of trails, gradually becoming interconnected as part of the Mystic Greenways initiative.

8. Sanborn House

A notable example of residential architecture in Winchester, the Sanborn House is a rare surviving country estate, constructed in the Beaux-Arts style in 1906. Originally the home of Oren Sanborn, son of James Sanborn, co-founder of the Chase & Sanborn Coffee Company. The estate was preserved after being sold in 1920 to the Religious of Christian Education, which established a grade school on the premises.

This eventually evolved into Ambrose Elementary School, which relocated to a new adjacent facility in 2003, allowing the Winchester Historical Society to undertake a comprehensive restoration of the Sanborn House. The interior is open for viewing on Tuesdays, Wednesdays, and Thursdays, while during winter, the lawn transforms into a favored sledding hill for local children.

9. Horn Pond Recreation Area

The endpoint of the Tri-Community Greenway leads to a 102-acre pond, bordered by wooded parkland to the south and west. Visitors can walk or jog around the entire circumference of Horn Pond on a paved trail, and it is worthwhile to find a bench along Arlington Rd on the east side to enjoy the sunset over the water.

Summer presents a great opportunity to visit the pond, as Boating in Boston offers kayak rentals (both single and double) by the hour. Additionally, if you possess your own non-motorized vessel, there are public boat launches accessible on both the southern and northern shores.

10. Horn Pond Mountain (Mt. Towanda)

Overlooking the southern side of Horn Pond is a prominent hill, while still classified within Woburn, it is enveloped on three sides by Winchester land. In the mid-20th century, Horn Pond Mountain was home to a ski resort, with faint traces of the chairlifts still recognizable amidst the vegetation. If time permits, a scenic loop trail from the southern shore of the pond leads to the summit, where additional viewpoints of the Boston skyline are available on the southeastern side.

11. Winchester Farmers’ Market

Every Saturday morning until the end of October, a farmer’s market takes place at the Town Common. As of the writing of this article, the market featured approximately ten permanent vendors alongside a larger contingent of part-time vendors, with weekly updates provided by the organizers on social media platforms.

Shoppers can explore a variety of locally sourced products, including fruits and vegetables from Wright-Locke Farm, as well as sustainable seafood, pasture-raised meats, maple syrup, eggs, tea blends, different types of breads, pastries, and artisanal candies. A range of prepared food options is also available, offering selections from stews and flatbreads to Chinese dumplings and unique Congolese dishes.

12. The Brooks Estate

In 1880, Shepherd Brooks (1837-1922), a member of a prominent Medford family, commissioned the Peabody & Stearns firm to construct an extravagant Queen Anne mansion on an estate exceeding 80 acres. Presently owned by the town, efforts are underway to restore the manor house, and visitors are welcome to explore the grounds.

Set against the backdrop of exquisite Victorian architecture, the estate features wetlands, a pond, and mature stands of maple and oak trees, with trails that connect to Winchester’s Brooks-Parkhurst Town Forest, providing an extended opportunity for walking in nature.

13. Whipple Hill

The trails from Wright-Locke Farm extend into a 120-acre conservation area belonging to Lexington. The summit of Whipple Hill stands as the highest point in the town, reaching an elevation of 375 feet, and the surrounding landscape encompasses mature hardwood and pine forests, rocky outcrops, wetlands and the lush banks of Whipple Brook.

The peak, located at the north end, can be accessed via the red-blazed Geology Loop, and there also exists a Farm/Wetland Loop that connects with Wright-Locke Farm, a Conservation Trail, and a portion of Lexington’s ACROSS trail system.

14. Winter Pond

Winter Pond, one of Winchester’s larger bodies of water, is easily overlooked, located at the foot of Horn Pond Mountain on the town’s west side. This kettle hole pond, formed by glacial activity during the last Ice Age, has Woodside Road dividing it into larger and smaller sections. A makeshift parking area is available along the road.

A kiosk and a bench are present, allowing visitors to pause and appreciate one of the most picturesque scenes in town, particularly delightful at sunset.

15. Photoville Fence

Now a celebrated annual event, this summer pop-up exhibition is a collaboration between the Griffin Museum, Photoville, and the Winchester Cultural District. Typically launching in June, the Photoville Fence is primarily set up along the shores of Judkins Pond adjacent to the museum building.

Here, attendees will engage with a series of photographic installations highlighting the work of regional, national, and international contemporary photographers. Recent projects have seen partnerships with various institutions, businesses, and publications, including the United Nations, Leica Camera USA, and Atlantic Magazine.