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Road cycling routes
United States
Connecticut
Southeastern Connecticut Planning Region
Mystic

Watch Hill Point – Maschaug Pond loop from Mystic

Moderate

4.9

(3821)

13,583

riders

Watch Hill Point – Maschaug Pond loop from Mystic

03:47

87.1km

510m

Road cycling

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride. The starting point of the route is accessible with public transport.

Last updated: May 13, 2026

Tips

Includes a segment in which cycling is not permitted

After 69.5 km for 76 m

Waypoints

A

Start point

Train Station

Get Directions

1

2.74 km

Quiambog Cove

Highlight • Beach

Quiambog Cove borders the ocean where Long Island and Block Island Sounds intersect. The cove can be accessed by the public at Knox Preserve.

Tip by

13.6 km

Parker Brothers Preserve

Nature Reserve

3

28.5 km

Napatree Point

Highlight • Beach

Napatree Beach and Peninsula is a very picturesque and charming place. Busy in summer time, on one side you can see all the moored boats and on the other side …

Translated by Google •

Tip by

4

29.1 km

Watch Hill Point

Highlight • Viewpoint

Watch Hill is the southwesternmost point of Rhode Island. Here in the small village you will also find a lighthouse, a beach and a great view of the ocean and Long Island.

Tip by

5

31.8 km

Maschaug Pond

Highlight • Lake

Maschaug Pond is a coastal lagoon, renowned as a popular birding area. What makes it particularly unique is that the only thing separating this body of water from the ocean …

Tip by

6

38.5 km

Fenway Beach

Highlight • Beach

Fenway Beach is a small sandy beach next to the jetty and canal. It is a popular spot for sunbathing, swimming, and surfing. The rocks on the east side can …

Tip by

7

39.2 km

Weekapaug Overlook

Highlight • Viewpoint

Weekapaug Overlook is an elevated overlook, with some roadside parking, overlooking the rocky shore of the Atlantic Ocean on Spray Rocks Road. It is a great spot to catch the sunrise (or sunset).

Tip by

8

57.5 km

Revive Coffee Van

Highlight • Cafe

Great coffee, only open on weekends

Tip by

68.5 km

Babcock Road Pond

Lake

69.6 km

Stephen Main Homestead

Nature Reserve

11

86.4 km

Mystic River Bascule Bridge

Highlight • Bridge

For cyclists crossing the Mystic River Bascule Bridge, the view is nothing short of captivating. From this vantage point, you're treated to a picturesque scene of the serene Mystic River …

Tip by

B

87.1 km

End point

Train Station

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Way Types & Surfaces

Way Types

57.7 km

16.9 km

11.9 km

406 m

184 m

Surfaces

71.2 km

15.6 km

339 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 (80 m)

Lowest point (0 m)

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Weather

Powered by Foreca

Today

Thursday 25 June

24°C

15°C

0 %

Additional weather tips

Max wind speed: 14.0 km/h

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Description

If you're looking for a road cycling route that truly delivers on New England coastal charm, the Watch Hill Point – Maschaug Pond loop from Mystic is an excellent choice. This moderate route covers 54.1 miles (87.1 km) with 1670 feet (509 metres) of elevation gain, typically taking around 3 hours and 47 minutes. It's ideal for cyclists who appreciate diverse scenery and a good workout without extreme climbs, offering a rewarding journey through picturesque landscapes.

What to expect on Watch Hill Point – Maschaug Pond loop from Mystic

The route unfolds as a scenic journey, starting from Mystic and guiding you through charming coastal villages, past serene salt marshes, and alongside sandy beaches. You'll experience stunning ocean vistas, particularly around Watch Hill Point, the southwesternmost tip of Rhode Island, where you can spot the historic Watch Hill Lighthouse. The terrain is generally flat to gently rolling, though you should be prepared for some classic New England hills that add a bit of challenge. While much of the route is well-paved asphalt, some longer sections in the wider area might include unpaved segments, so be aware of changing surfaces. This ride suits a range of cyclists, from those looking for a leisurely tour to more experienced riders seeking a moderate distance with varied views.

Planning your visit

Starting from Mystic, you'll find this loop easily accessible. Local bike shops in Mystic often highlight similar routes that connect to the Watch Hill and Misquamicut areas, suggesting good starting points. While specific parking details aren't provided, Mystic offers various options for parking your vehicle before you set off. The area's beauty is best enjoyed during pleasant weather, so check the forecast before you go. No special permits or fees are mentioned for this route, making it straightforward to plan your ride.

Trail details

  • Distance: 54.1 miles (87.1 km)
  • Elevation gain: 1670 feet (509 metres)
  • Difficulty: moderate
  • Estimated time: 3 hours and 47 minutes

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