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Routes
Road cycling routes
United States
Massachusetts
Norfolk County
Wellesley

Wellesley Hills to Borderland State Park loop via Seekonk Street

Routes
Road cycling routes
United States
Massachusetts
Norfolk County
Wellesley

Wellesley Hills to Borderland State Park loop via Seekonk Street

Moderate

4.8

(1081)

17,258

riders

Wellesley Hills to Borderland State Park loop via Seekonk Street

03:31

84.7km

600m

Road cycling

This moderate road cycling route from Wellesley Hills offers a substantial ride, covering 52.6 miles (84.7 km) with 1968 feet (600 metres) of elevation gain. You will experience a scenic transition from leafy suburban streets to more rural Massachusetts landscapes, passing through wooded sections and open fields. Keep an eye…

Last updated: April 23, 2026

Waypoints

A

Start point

Parking

Get Directions

1

18.9 km

Seekonk Street

Highlight (Segment) • Cycleway

Cruise along this lovely road and catch your breath!

Tip by

2

49.6 km

Borderland State Park Forest

Highlight • Forest

Borderland State Park is a nature reserve that includes trails, a lake, and the historic Ames Mansion. The park is open for many activities such as horse back riding, cycling, hiking, cycling and water activities on the lake.

Tip by

3

68.1 km

Willett Pond

Highlight • Lake

Willett Pond is a small lake with a small beach area where kayaking is also allowed. The residents of the 85 houses there are allowed to use the lake more, but also protect it. An exciting and good concept.

Tip by

B

84.7 km

End point

Parking

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Way Types & Surfaces

Way Types

68.7 km

11.1 km

4.89 km

< 100 m

Surfaces

83.7 km

996 m

< 100 m

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Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (110 m)

Lowest point (30 m)

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Weather

Powered by Foreca

Today

Sunday 31 May

19°C

3°C

45 %

Additional weather tips

Max wind speed: 19.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

How difficult is the Wellesley Hills to Borderland State Park road cycling route?

This route is classified as moderate. It covers approximately 84.7 kilometers (52.6 miles) with an elevation gain of about 600 meters (1,968 feet). While mostly paved, be prepared for rolling hills and potentially some unpaved or less-than-perfect road segments, requiring a good level of fitness.

Is this route suitable for beginner road cyclists?

Given its moderate difficulty, distance, and elevation gain, this route is generally better suited for cyclists with some experience. Beginners might find the length and varied terrain challenging. Consider shorter, flatter routes to build endurance before tackling this loop.

What is the terrain like on this cycling route?

The route primarily consists of well-paved roads, ideal for a racebike. However, be aware that some segments may be unpaved and difficult to ride, potentially including gravel sections. The elevation profile features noticeable ascents and descents throughout, indicating rolling hills rather than sustained steep climbs.

What scenic spots or landmarks can I expect to see along the way?

You'll experience a transition from suburban Wellesley Hills to more rural landscapes as you approach Borderland State Park. Key highlights include cycling along Seekonk Street, passing through Borderland State Park Forest, and views of Willett Pond. Borderland State Park itself offers natural beauty and historic buildings like the Ames mansion, though most trails within the park are not suitable for road bikes.

What is the best time of year to cycle this loop?

The best time to cycle this route is typically from late spring through early fall (May to October). During these months, the weather is generally mild, and road conditions are most favorable. Avoid winter months due to potential ice and snow, and be mindful of hot summer days.

Where can I park to access this cycling route?

As this is a loop starting from Wellesley Hills, you would typically find parking in or around Wellesley Hills. Specific parking details for the start of the loop are not provided, but public parking areas in Wellesley or near the route's initial segments would be suitable. Always check local parking regulations.

Are there any permits or entrance fees required for this route, especially at Borderland State Park?

Cycling on public roads along the route does not require permits or fees. However, if you plan to stop and enter Borderland State Park, there may be parking fees or day-use fees, especially for vehicles. Check the official mass.gov website for Borderland State Park for current fee information and regulations.

Is the Wellesley Hills to Borderland State Park loop dog-friendly?

While the cycling route itself is on public roads, Borderland State Park is generally dog-friendly, but specific rules apply. Dogs must be kept on a leash at all times and are not allowed in buildings or swimming areas. Always clean up after your pet. For detailed regulations, consult the Borderland State Park website.

What kind of bike and gear should I bring for this ride?

This route is designed for a racebike. Given the potential for some unpaved or rough segments, ensure your tires are in good condition and consider slightly wider tires if you're concerned about mixed terrain. Always bring a helmet, water, snacks, a repair kit, and navigation tools. Layered clothing is recommended due to varying temperatures over the distance.

Does this route intersect with other well-known trails?

Yes, while primarily a road cycling route, it briefly intersects with or runs parallel to several other paths. You may encounter sections of the Bay Circuit Trail, Warner Trail, and the Massapoag Trail, among others, though these are typically hiking or mountain biking trails and not suitable for road bikes.

Are there places to stop for food or drinks along the route?

Wellesley Hills offers various cafes and restaurants at the start or end of your ride. As you venture towards Borderland State Park, options become more sparse, but you may find establishments in towns like Sharon or Easton, which are near the park. It's advisable to carry sufficient water and snacks, especially for the middle sections of the loop.

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