Jennings Pond – Bushnell-Dickinson House loop from Middlesex County

Lower Connecticut River Valley Planning Region

Jennings Pond – Bushnell-Dickinson House loop from Middlesex County

Moderate

2.9

(1)

riders

Jennings Pond – Bushnell-Dickinson House loop from Middlesex County

04:10

89.4km

730m

Road cycling

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride. The starting point of the route is right next to a parking lot.

Last updated: August 20, 2026

Tips

The surface along some of this route may not be suitable

Some segments of your route comprise a surface that may not be suitable for your chosen sport.

After 18.3 km for 2.03 km

After 72.4 km for 93 m

Waypoints

Start point

Parking

Get Directions

13.3 km

Village Green

Nature Reserve

14.5 km

Jennings Pond

Highlight • Lake

Jennings Pond is a pond created by a small dam on the eastern side of the pond which sits between two private properties. The pond is surrounded by trees and …

Tip by

20.4 km

Shailer Pond

Lake

33.2 km

Town Open Space (West Pond Meadow Road)

Nature Reserve

41.7 km

Bushnell-Dickinson House

Highlight • Historical Site

Listed on the National Register of Historic Places in 1978, this house was first constructed in 1790. It was once on the main east–west road through Old Saybrook, offering some pretty historic views.

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47.3 km

Original location of Yale College

Highlight • Historical Site

Right across from the Cypress Cemetery, a historic spot in its own right, is the original location of Yale College. There is a large stone with a plaque and an informational sign marking the spot.

Tip by

50.8 km

Knollwood Beach

Highlight • Beach

You'll often see people fishing at Knollwood Beach as it has the reputation of being an excellent spot for a successful catch.

Tip by

53.7 km

View of Back River from Great Hammock Road

Highlight (Segment) • Viewpoint

Great Hammock Road is one of many beautiful waterside roads in the area. It passes over Back River with views west towards Oyster Point and Indian Town Harbour and east towards Dunks Island.

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67.0 km

River Road

Highlight (Segment) • Viewpoint

River Road, along with a few of the other paved roads and bridges in the area, offers views of the Connecticut River. There are a bunch of neighborhoods on the …

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72.4 km

Evelyn & Hawthorne Smyth Sanctuary

Highlight • Lake

Evelyn & Hawthorne Smyth Sanctuary is a small nature Preserve off of Essex Street near Post Cove and the Connecticut River. As you ride, you get nice views over the water in this attractive area.

Tip by

73.6 km