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Routes
Road cycling routes
United States
Massachusetts
Barnstable County
Dennis Port

Pleasant Lake (Hinckleys Pond) – Seymour Pond loop from Dennis Port

Routes
Road cycling routes
United States
Massachusetts
Barnstable County
Dennis Port

Pleasant Lake (Hinckleys Pond) – Seymour Pond loop from Dennis Port

Moderate

4.5

(6239)

6,350

riders

Pleasant Lake (Hinckleys Pond) – Seymour Pond loop from Dennis Port

02:37

66.5km

230m

Road cycling

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride. The starting point of the route is right next to a parking lot.

Last updated: May 18, 2026

Waypoints

A

Start point

Parking

Get Directions

4.36 km

Lothrop Avenue Conservation Area

Nature Reserve

2

9.56 km

Pleasant Lake (Hinckleys Pond)

Highlight • Lake

Hinckleys Pond is also known as Pleasant Lake and is classified as a Great Pond due to its 172-acre size. It has a well-maintained beach with plenty of activities. The …

Tip by

3

10.6 km

Long Pond

Highlight • Lake

Long Pond is huge freshwater pond in Brewster and Harwich (the town line crosses down the middle of it). The Cape Cod Rail Trail runs right along the western shore …

Tip by

4

11.1 km

Seymour Pond

Highlight • Lake

Seymour Pond is one of many freshwater kettle ponds in the Brewster/Harwich area. The public beach for this scenic pond butts right up against the Cape Cod Rail Trail and …

Tip by

5

12.5 km

Sheep's Pond

Highlight • Lake

Sheep's Pond is a small kettle pond in Brewster, Massachusetts. This pretty pond is right down a steep hill from the Cape Cod Rail Trail and has a pretty, but …

Tip by

6

19.0 km

This spot is where you can access Nickerson State Park from the Cape Cod Rail Trail in Brewster. Just a short distance west of here along the trail there is …

Tip by

7

24.0 km

Cedar Pond

Highlight • Lake

The East Coast Greenway meets the road here at Cedar Pond so it's a good place to join the bike path if you're in Orleans.

Tip by

8

24.5 km

Cape Cod Rail Trail (Orleans to Eastham)

Highlight (Segment) • Cycleway

This section of the popular, multi-use Cape Cod Rail Trail runs from downtown Orleans to Eastham. This is a general flat, easy section of riding, but it can get very, …

Tip by

33.2 km

Viewpoint

Viewpoint

10

61.3 km

Cape Cod Rail Trail (Bell's Neck Segment)

Highlight (Segment) • Cycleway

The short segment of the Cape Cod Rail Trail skirts Bells Neck Conservation Lands and overlooks the water. You can often see swans, geese, and other birds, as well as turtles and frogs from the bike trail.

Tip by

B

66.5 km

End point

Parking

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Way Types & Surfaces

Way Types

56.1 km

7.69 km

2.30 km

444 m

< 100 m

Surfaces

66.0 km

434 m

113 m

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Elevation

Elevation

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

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Weather

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Today

Monday 13 July

24°C

16°C

0 %

Additional weather tips

Max wind speed: 22.0 km/h

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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

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Description

The Pleasant Lake (Hinckleys Pond) – Seymour Pond loop from Dennis Port is a fantastic choice if you're looking for a scenic and accessible road cycling route on Cape Cod. This moderate 41.3-mile (66.5 km) ride, with a gentle 766 feet (233 metres) of elevation gain, can be completed in about 2 hours and 37 minutes, making it perfect for a rewarding half-day adventure that showcases the region's natural beauty.

What to expect on Pleasant Lake (Hinckleys Pond) – Seymour Pond loop from Dennis Port

Expect a smooth ride on mostly well-paved surfaces, often integrating with the Cape Cod Rail Trail, which keeps you away from traffic. The route unfolds through picturesque pond-dotted landscapes, offering views of both Pleasant Lake (Hinckleys Pond) and the crystal-clear waters of Seymour Pond, especially beautiful at sunset. You'll also pass through diverse Cape Cod scenery, including pine forests and cranberry bogs, with minimal elevation changes making it suitable for nearly any cyclist.

Planning your visit

This loop is a popular choice among local road cyclists in the Dennis Port area, known for its accessibility and well-maintained paths. Since the route is generally flat and well-paved, it's a great option for road cycling Dennis Port throughout the warmer months. There are no specific permits or fees mentioned, so you can simply arrive and enjoy the ride.

Trail details

  • Distance: 41.3 miles (66.5 km)
  • Elevation gain: 766 feet (233 metres)
  • Difficulty: moderate
  • Estimated time: 2 hours and 37 minutes

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