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Routes
Bike touring routes & trails
United States
Massachusetts
Suffolk County
Winthrop

Deer Island southernmost tip – Deer Island loop from Winthrop Highlands

Routes
Bike touring routes & trails
United States
Massachusetts
Suffolk County
Winthrop

Deer Island southernmost tip – Deer Island loop from Winthrop Highlands

Easy

4.8

(5812)

9,795

riders

Deer Island southernmost tip – Deer Island loop from Winthrop Highlands

00:58

16.7km

70m

Cycling

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

Last updated: July 21, 2025

Waypoints

A

Start point

Bus stop

Get Directions

1

5.96 km

Deer Island viewpoint

Highlight • Viewpoint

2

6.89 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 …

Tip by

3

9.38 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 …

Tip by

4

11.6 km

Winthrop Beach

Highlight • Beach

Clean and quiet beach in Winthrop. The five large offshore breakwaters – known as „the Five Sisters” keep the water pretty calm.

Tip by

B

16.7 km

End point

Bus stop

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Way Types & Surfaces

Way Types

10.1 km

4.25 km

2.31 km

< 100 m

Surfaces

14.4 km

2.27 km

< 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

Powered by Foreca

Today

Friday 26 June

24°C

19°C

78 %

Additional weather tips

Max wind speed: 20.0 km/h

to get more detailed weather forecasts along your route

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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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