Rock Square via Portland Road loop
Rock Square via Portland Road loop
5.0
(9014)
10,651
riders
00:56
16.2km
60m
Cycling
This easy 10.1-mile touring cycling loop in Kennebunk offers coastal views, charming towns, and passes by Dock Square in under an hour.
Last updated: February 26, 2026
Waypoints
Start point
Parking
Get Directions
7.52 km
Highlight • Settlement
Tip by
16.2 km
End point
Parking
Way Types & Surfaces
Way Types
7.58 km
6.73 km
1.91 km
< 100 m
Surfaces
10.5 km
5.49 km
234 m
Sign up to see more specific route details
Sign up for free
Elevation
Sign up to see more specific route details
Sign up for free
Weather
Powered by Foreca
Sunday 12 July
27°C
14°C
0 %
Additional weather tips
Max wind speed: 11.0 km/h
to get more detailed weather forecasts along your route
This route was planned by komoot.
This loop is rated as easy, making it suitable for most fitness levels. With an elevation gain of approximately 57 meters over its 16.2-kilometer distance, it offers a pleasant touring bicycle experience without significant climbs.
You can expect a varied terrain on this loop. While specific details for this exact route are not available, similar touring bicycle routes in the Kennebunk area often feature a mix of paved roads and potentially some crushed stone or asphalt sections. Given its easy rating, it's likely to be mostly well-maintained surfaces.
The best times to cycle this loop are generally spring, summer, and fall. These seasons offer pleasant weather for touring cycling, allowing you to fully enjoy the coastal scenery and charming New England towns. Summer can be popular, so spring and fall might offer a more tranquil experience.
Yes, the route passes through Dock Square, a notable highlight. Additionally, as the loop incorporates Portland Road, you'll likely encounter scenic coastal views, charming historic homes, and potentially glimpses of salt marshes or wooded areas typical of the Kennebunk region.
While the loop primarily uses roads and potentially some multi-use paths, specific dog regulations can vary. Generally, dogs on a leash are welcome on many public paths and roads in the Kennebunk area. Always ensure your dog is well-behaved and that you clean up after them.
For parking, consider public parking areas in Kennebunk or Kennebunkport, especially near Dock Square or other central locations. Many towns offer designated parking lots that provide convenient access to local cycling routes. Always check local signage for parking restrictions and fees.
No, you do not need any special permits or pay entrance fees to cycle the Rock Square via Portland Road loop. It primarily utilizes public roads and potentially existing multi-use paths, which are generally free to access for recreational cycling.
Yes, this route briefly intersects with other paths. You'll find it passes through small sections of the James Woods Trail, the Welch Woods Trail, and The Secret Garden. These intersections might offer short detours or connections to explore more of the local area.
Given its 'easy' difficulty rating and relatively flat profile, the Rock Square via Portland Road loop is generally suitable for families. For even flatter, dedicated paths, the nearby Bridle Path in Kennebunk is an excellent flat dirt path, perfect for beginners and families.
As the loop passes through Dock Square and utilizes Portland Road, you'll find numerous cafes, restaurants, and pubs in the charming towns of Kennebunk and Kennebunkport. These areas offer plenty of opportunities to stop for a meal, a coffee, or a refreshing drink.
Winter cycling on this loop is possible but requires caution. Roads may be icy or covered with snow, and conditions can be unpredictable. If cycling in winter, ensure your bike is equipped for cold weather, wear appropriate gear, and check local weather and road conditions before heading out.
Comments
Want to know more?
Sign up for a free komoot account to join the conversation.
Sign up for free