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Bike touring routes & trails

Deer Island southernmost tip – Deer Island loop from Aquarium

Routes

Bike touring routes & trails

Deer Island southernmost tip – Deer Island loop from Aquarium

Easy

3.1

(15)

riders

Deer Island southernmost tip – Deer Island loop from Aquarium

01:46

29.3km

90m

Cycling

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels. The route includes a crossing by ferry. The starting point of the route is accessible with public transport.

Last updated: July 21, 2025

This route includes a ferry crossing

Tips

Cycling is not permitted along parts of this route

After 17.4 km for 170 m

After 26.6 km for 247 m

Waypoints

Start point

Train Station

Get Directions

2.95 km

Bremen Street Park

Highlight • Rest Area

Bremen Street Park is a great green park in the urban environment of East Boston. The park is a buffer between Longan airport and the residents of East Boston.

The park has a large public lawn, a shared use path and a playground.

Tip by

5.20 km

Constitution Beach

Highlight • Beach

Constitution Beach is a man-made beach that was opened to the public in 1952. Its proximity to two area airports make it a great location to see airliners at take off and landing. There are also a host of amenities including a shower block, refreshment stand, and public walkway.

Tip by

11.0 km

Point Shirley Beach

Beach

13.5 km

Deer Island southernmost tip

Highlight (Segment) • Viewpoint

I've been going to Deer Island once a month for roughly 10 years now. It's truly the most underappreciated space in the whole metro Boston area. On the one side you have the outer harbor with views up to Cape Ann, Graves Light, and Boston light. At the southern tip, the main entrance to Boston Harbor, you turn the corner to see Boston's skyline in the distance. It's where the two sides come together. Really a standout place to visit, especially for a summer sunset. The only downside is parking has become a real serious challenge in recent years.

Tip by

14.9 km

Deer Island viewpoint

Highlight • Viewpoint

15.8 km

Deer Island

Highlight • Historical Site

This isn't an island anymore, but a wonderfully scenic peninsula; it became connected to the mainland in 1938 when beach erosion filled in the channel that had previously separated the island from Winthrop. nowadays, you can pedal a roughly 2.5-mile loop around the "island" (the tip of the peninsula) and enjoy wonderful views out over the water.

Deer Island is also designated as a historical place by the National Park Service, due to its use as an internment site for indigenous people during King Philip's War; you can read about that history here: nps.gov/places/deer-island.htm

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