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Routes
Bike touring routes & trails
United States
Maine
Waldo County

Isleboro Island South loop

Easy

2.9

(21)

84

riders

Isleboro Island South loop

01:32

26.5km

150m

Cycling

Cycle the easy 16.5-mile Isleboro Island South loop, enjoying coastal views, rolling hills, and landmarks like Grindel Point Light.

Last updated: February 26, 2026

Waypoints

A

Start point

Ferry Terminal

Get Directions

1

85 m

Grindel Point Light

Highlight • Monument

The current lighthouse and keepers quarters were built in 1874 and continuously operated until 1934. The lighthouse was decommissioned in the 1930s only to resume operations just over 50 years …

Tip by

2

7.19 km

Dark Harbor

Highlight • Settlement

Despite its ominously cool name, that evokes the horrors of a Stephen King novel, Dark Harbor is actually known as a pleasant summer retreat.

Tip by

3

11.0 km

Pendleton Point

Highlight • Viewpoint

Located at the southern tip of Islesboro Island, Pendleton Point has great views over the rocks and across the water.

Tip by

B

26.5 km

End point

Ferry Terminal

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Way Types & Surfaces

Way Types

25.8 km

692 m

Surfaces

25.8 km

659 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

Powered by Foreca

Today

Friday 5 June

27°C

11°C

30 %

Additional weather tips

Max wind speed: 19.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

How do I get to the start of the Isleboro Island South loop, and where can I park?

To begin this cycling route, you'll first need to take the ferry from Lincolnville to Isleboro Island. Parking is available at the ferry terminal in Lincolnville. Once on the island, the loop starts near the ferry landing.

Is this cycling route dog-friendly?

While the island itself is generally welcoming, specific rules for dogs on cycling routes can vary. It's best to keep dogs leashed and ensure they are comfortable with cycling alongside you, especially given the narrow, winding roads. Always clean up after your pet.

What is the best time of year to cycle the Isleboro Island South loop?

The best time to cycle this route is typically from late spring through early autumn. During these months, the weather is most pleasant for cycling, and the island's natural beauty is at its peak. Summer offers warmer temperatures, while spring and fall provide cooler rides and beautiful foliage.

Are there any permits or entrance fees required for this route?

No, there are no specific permits or entrance fees required to cycle the Isleboro Island South loop itself. However, you will need to pay a fare for the ferry service to reach the island.

Is the Isleboro Island South loop suitable for beginners?

Yes, this route is generally classified as an easy bike ride, making it suitable for most fitness levels and beginners. It features mostly paved surfaces and manageable elevation changes, typically involving around 150 meters (500 feet) of gain over its 26.5 km distance.

What kind of terrain can I expect on this cycling route?

The route primarily features paved surfaces, making it accessible for touring bicycles. While not entirely flat, you'll encounter rolling hills and winding, narrow roads, some shaded by trees. The total distance is approximately 26.5 km.

What points of interest will I see along the Isleboro Island South loop?

Along the route, you'll encounter several notable spots. These include the historic Grindel Point Light, the pleasant summer retreat of Dark Harbor, and Pendleton Point, which offers excellent views over the rocks and water.

How long does it typically take to complete this cycling loop?

The Isleboro Island South loop is designed to be completed in approximately 1 hour and 32 minutes of active cycling time. This duration is for the 26.5 km route with an easy difficulty grading.

Is the Isleboro Island South loop a good option for family cycling?

Yes, given its easy difficulty and mostly paved surfaces, this loop can be a good option for families. The relatively low traffic on the island's narrow roads contributes to a peaceful cycling environment, though islanders driving to the ferry can be time-sensitive.

Can I rent a bicycle on Isleboro Island?

While Isleboro Island is a popular cycling destination, specific bike rental services directly on the island are not widely advertised. It's recommended to bring your own bicycle or inquire about rentals in nearby mainland towns before taking the ferry.

Are there places to eat or get refreshments along the route?

Isleboro Island has a few establishments, particularly in areas like Dark Harbor, where you might find cafes or small eateries. However, options can be limited, especially outside of peak season. It's always a good idea to bring your own snacks and water.

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