4.0
(2)
42
riders
5
rides
Touring cycling routes around Eastport offer a blend of rugged coastal beauty and diverse natural features. The region is characterized by its location on Passamaquoddy Bay, providing ocean views and a picturesque waterfront with a rugged, windswept coastline. Cyclists can expect a mix of road and carriage trail surfaces, including rural chip-and-seal pavement, with some sections featuring gravel or hard-packed dirt. The terrain often includes rolling hills and short, steep climbs, reflecting the dynamic seascapes influenced by the Bay of…
Last updated: May 16, 2026
3.0
(1)
17
riders
43.8km
02:29
80m
80m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
7
riders
52.7km
03:04
190m
190m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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6
riders
28.8km
01:37
30m
30m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
2
riders
168km
09:36
590m
590m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5
riders
19.8km
01:08
20m
20m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Eastport
Canoe Place is a luxury resort town on the Shinnecock Canal with upscale hotels, restaurants, and water access. The Paumanok Path passes through the center of town, and on some maps detours down Gate Street to the canal, where there is often a porta potty, and where you can get excellent views of the canal bridge.
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An unbelievable view. Please take use that way and see yourself
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Dune Road spans over 14 miles, drawing a straight line down the island from Cupsogue Beach to Ponquogue State Park. Your views of the scenic shoreline and Hampton beach homes are uninterrupted the entire way. There isn't much shoulder, but you generally won't find too much traffic and this makes for a great way to explore the island.
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These are the famous beaches in the Haptons just before the huge ostentatious villas begin. It is simply a dream, every time I am here my heart beats faster
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From this spot on Dune Road you get a fantastic view of the bay and marshes on one side and the vast Atlantic on the other. This is a great bit of riding in the Hampton Bays.
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The Shinnecock Canal was the first saltwater canal in New York State, built between 1884 and 1892. Once a site used by Native Americans to carry canoes over land, the Canal today connects two of the most stunning bays on Long Island's eastern side, Shinnecock Bay and Great Peconic Bay, which had become landlocked over time. Though the Hamptons officially begin 10 miles (16.09 km) west of the Canal, it is known as the starting point of this exclusive summer resort, as every modern bridge leading to the Hamptons crosses the Canal.
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Built in 1920, this carousel is one of the few remaining with a brass ring game where rings are dispensed to riders during the ride. Riders grab the brass ring among the iron rings for a chance to win a prize from the operator. Visitors test their skills and play a 100 year old game.
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Arshamomaque Cemetery, also known as the Hashamomack Old Families' Burying Ground, is open to the public and a great spot to stop by and check out some of the oldest graves on Long Island. Here lie settlers from the 17th, 18th, and 19th centuries, and the oldest known grave here is over 200 years old.
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Touring cycling around Eastport offers a diverse mix of surfaces. You'll encounter rural chip-and-seal pavement, as well as sections of gravel and hard-packed dirt, particularly on trails like the Down East Sunrise Trail. The landscape features rolling hills and short, steep climbs, reflecting the dynamic coastal environment influenced by the Bay of Fundy's high tides.
Yes, Eastport offers routes suitable for beginners. For instance, the Bike loop from Village of Westhampton Beach is an easy 14.5 km ride. Another accessible option is the Dune Road – Dune Road loop from Village of Westhampton Beach, which covers 28.8 km with minimal elevation changes.
Eastport's routes are rich with scenic views. You can expect stunning ocean vistas along Passamaquoddy Bay and picturesque waterfronts. The region is known for its rugged, windswept coastline and the dramatic tides of the Bay of Fundy. While cycling, you might spot the impressive Old Sow Whirlpool or enjoy views of Cobscook Bay and Campobello Island. Nearby parks like Shackford Head State Park and Quoddy Head State Park offer spectacular overlooks and diverse landscapes including coastal forests and peat bogs.
While specific 'family-friendly' designations for all routes aren't available, the region offers options that can be enjoyed by families. Shorter, easier routes like the Bike loop from Village of Westhampton Beach are generally suitable. The Down East Sunrise Trail, an 87-mile off-road trail, has sections of gravel and hard-packed dirt that can be explored for shorter distances, offering a safe, car-free environment through marshes and coastal villages.
The best time for touring cycling in Eastport is generally during the warmer months, from late spring through early autumn. This period offers more favorable weather conditions, allowing cyclists to fully appreciate the coastal scenery and natural features. It's advisable to check local weather forecasts, especially regarding coastal winds and potential 'mud season' conditions in early spring, which might affect unpaved trails.
Yes, many of the touring cycling routes around Eastport are designed as loops. For example, the Ponquogue Bridge View – Dune Road loop from Westhampton and the Dune Road – Dune Road loop from Westhampton are popular circular options, allowing you to start and end your ride in the same location.
The Eastport region is rich in wildlife. While cycling, especially near coastal areas and preserves like Cobscook Bay State Park, you might spot eagles, seals, and porpoises. The area is also excellent for bird-watching, and during certain times, even whales can be seen from coastal viewpoints, adding to the natural adventure.
Yes, the Eastport area is home to several points of interest. Near some routes, you can explore places like Grumman Memorial Park or enjoy the natural beauty of Terrell River County Park. The Vietnam Veterans Memorial Recreational Trail also offers a unique experience. Further afield, the iconic West Quoddy Head Lighthouse in Quoddy Head State Park is a must-see landmark.
The touring cycling routes in Eastport are highly rated by the komoot community, with an average score of 4.0 stars. Cyclists often praise the blend of rugged coastal beauty, the diverse natural features, and the variety of terrain that includes both paved roads and scenic carriage trails. The opportunity to experience the dramatic Bay of Fundy tides and explore picturesque waterfronts is also a significant draw.
For those seeking a challenge, Eastport offers more demanding routes. The Lake Agawam – Mitchell Park loop from Riverhead is a difficult 168.3 km trail with significant elevation changes, typically taking over 9 hours to complete. This route leads through diverse landscapes and is ideal for experienced touring cyclists looking for a long-distance adventure.
While Eastport is a relatively remote coastal town, public transport options directly to specific trailheads might be limited. It's generally recommended to plan your trip with personal vehicle access for parking near trail starts. However, for broader regional travel, you might find limited bus services connecting larger towns, but direct access to all cycling routes via public transport is not widely available.
Parking availability varies by route. For routes that start in or near towns like Westhampton, you can often find public parking areas. For state parks such as Shackford Head State Park or Quoddy Head State Park, dedicated parking lots are available for visitors. When planning your ride, it's advisable to check the specific starting point of your chosen route for the most convenient parking options.


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