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Routes
Road cycling routes
United States
Maine
Waldo County

Isleboro Island, Maine south loop

Easy

2.8

(10)

60

riders

Isleboro Island, Maine south loop

01:05

26.4km

150m

Road cycling

Enjoy an easy 16.4-mile road cycling loop on Isleboro Island, Maine, featuring coastal views and landmarks like Pendleton Point.

Last updated: February 26, 2026

Waypoints

A

Start point

Ferry Terminal

Get Directions

1

100 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

10.9 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

14.7 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

26.4 km

End point

Ferry Terminal

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Way Types & Surfaces

Way Types

26.4 km

< 100 m

Surfaces

26.4 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

Saturday 6 June

15°C

10°C

59 %

Additional weather tips

Max wind speed: 18.0 km/h

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Frequently Asked Questions

How long does it typically take to cycle the Isleboro Island South Loop?

The Isleboro Island South Loop is a road cycling route that typically takes about 1 hour and 5 minutes to complete. This is based on an average cycling pace for the 26.4 km distance.

What is the difficulty level and terrain like for this cycling route?

The Isleboro Island South Loop is generally considered an easy road cycling route. While the island's terrain is described as 'rolling' and 'hilly' with some tree-shaded inclines, the primary route is mostly paved asphalt. You'll encounter an elevation gain of about 149 meters over the 26.4 km.

How do I get to Isleboro Island for cycling, and where can I park?

Isleboro Island is accessible by a 20-minute ferry ride from Lincolnville, Maine. The ferry schedule and cost should be checked in advance. Once on the island, parking is generally available near the ferry landing or other public areas, but specific parking instructions for the start of the loop are not detailed. The route itself starts and ends near the ferry terminal.

What scenic highlights and landmarks can I expect along the Isleboro Island South Loop?

The route offers majestic vistas of Penobscot Bay and captivating ocean views. Key highlights include the historic Grindel Point Light, which also houses the Grindel Point Sailor's Museum. You'll also pass through the charming settlement of Dark Harbor and reach Pendleton Point, a popular viewpoint at the southern tip of the island known for great views and potential harbor seal sightings.

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

The best time to cycle on Isleboro Island is typically during the warmer months, from late spring through early fall. This period offers pleasant weather for coastal cycling and allows you to fully enjoy the island's tranquil atmosphere and scenic beauty. Summer is popular, but can also be busier.

Is the Isleboro Island South Loop dog-friendly?

While the route is on public roads, specific regulations regarding dogs on the cycling route itself are not provided. If bringing a dog, it's advisable to ensure they are well-behaved, leashed, and that you are prepared to clean up after them. Always check local island rules regarding pets, especially concerning ferry travel and public spaces.

Are there any permits or entrance fees required to cycle on Isleboro Island?

There are no specific permits or entrance fees required to cycle on the roads of Isleboro Island. However, you will need to pay for the ferry service to access the island from Lincolnville.

Is the Isleboro Island South Loop suitable for families with children?

The Isleboro Island South Loop is an easy road cycling route, making it potentially suitable for families. However, be aware that the island's roads are described as narrow, shoulderless, and winding. While residents are generally tolerant of cyclists, families with younger or less experienced riders should exercise caution and consider the traffic conditions, especially during peak summer months.

Are there any specific considerations for cycling on Isleboro Island's roads?

Yes, it's important to note that Isleboro Island's roads are often narrow, lack shoulders, and can be winding. While the local community is increasingly aware of and tolerant towards cyclists, always ride defensively, be visible, and be prepared to share the road with vehicles. The island's tranquil nature means traffic is generally lighter than mainland routes, but caution is still advised.

Are there other cycling routes available on Isleboro Island besides the South Loop?

Yes, beyond the South Loop, the island offers options for a fuller cycling experience. A popular full island loop is approximately 28 miles (about 45 km), and some sources refer to a '30-mile route' option. These longer routes may include some unpaved segments, which could require good fitness or even necessitate pushing your bike.

Are there amenities like cafes or shops along the Isleboro Island South Loop?

Isleboro Island is a tranquil summer retreat, and while it has year-round residents and summer visitors, amenities like cafes and shops are limited, particularly along the cycling route itself. It's advisable to bring your own water and snacks, especially for the duration of the loop. The settlement of Dark Harbor might offer some limited options, but it's best to plan ahead.

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