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Routes
Running trails & routes
United States
Massachusetts
Barnstable County
South Dennis

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

Routes
Running trails & routes
United States
Massachusetts
Barnstable County
South Dennis

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

Hard

2.8

(13)

72

runners

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

02:00

19.2km

70m

Running

Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels. The starting point of the route is right next to a parking lot.

Last updated: April 20, 2026

Waypoints

A

Start point

Parking

Get Directions

1

2.25 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

2

7.88 km

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

8.90 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

9.39 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

16.2 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

19.2 km

End point

Parking

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Way Types & Surfaces

Way Types

18.5 km

485 m

< 100 m

Surfaces

17.9 km

1.15 km

< 100 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.

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Weather

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Today

Monday 6 July

21°C

17°C

68 %

Additional weather tips

Max wind speed: 18.0 km/h

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Description

If you're looking for a challenging yet rewarding jogging route on Cape Cod, the Pleasant Lake (Hinckleys Pond) – Seymour Pond loop from South Dennis delivers. This difficult 11.9-mile (19.2 km) route, with 232 feet (71 metres) of elevation gain, is designed to be completed in about 2 hours, making it a solid choice for those with very good fitness seeking a substantial workout amidst beautiful natural scenery.

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

This route offers a diverse experience, blending paved sections with more natural pond-side paths. You'll find yourself jogging along parts of the Cape Cod Rail Trail, which provides a smooth, mostly flat surface, before transitioning to trails that hug the shorelines of two picturesque natural kettle ponds: Pleasant Lake (Hinckleys Pond) and Seymour Pond. Keep an eye out for wildlife like swans, geese, and various birds, especially around the cranberry bogs and wooded areas. While the full loop is considered a hard run, sections, particularly the new flat and even "All Persons Trail" at Hinckleys Pond, are suitable for all skill levels if you prefer a shorter, more accessible outing.

Planning your visit

Access to both Pleasant Lake and Seymour Pond is conveniently available via the Cape Cod Rail Trail, which forms a significant part of this loop. There are no specific permits or fees mentioned for this route, and parking is generally available at various points along the Rail Trail or near the ponds. Given the length and difficulty, it's wise to start early in the day, especially during warmer months, to enjoy cooler temperatures and avoid peak crowds. Always carry enough water for the duration of your run.

Trail details

  • Distance: 11.9 miles (19.2 km)
  • Elevation gain: 232 feet (71 metres)
  • Difficulty: difficult
  • Estimated time: 2 hours

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