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United States
Connecticut
Lower Connecticut River Valley Planning Region

Portland

The best cycling routes around Portland

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Touring cycling around Portland offers diverse landscapes, from urban riverfront paths to routes through hills and forests. The region features extensive cycling infrastructure, including dedicated bike lanes and greenways. Cyclists can explore routes along the Willamette River, through urban parks, and into surrounding natural areas. The terrain varies from flat city sections to more challenging climbs in areas like Mount Tabor.

Best touring cycling routes around Portland

  • The most popular touring cycling route is Former Lyman Viaduct – Air Line…

Last updated: October 1, 2026

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#1.

Air Line Trail – Former Lyman Viaduct loop from East Hampton

62.3km

05:10

390m

390m

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Hard

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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5.0

(2)

13

riders

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

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Tips from the Community

Jamie S.
September 3, 2024, View of the River from Air Line State Park Trail (Southern Section)

The Air Line State Park Trail in Connecticut is a rail trail and linear state park that is a part of the East Coast Greenway. There are several sections including: South (25 miles from East Hampton to Windham), North (21 miles from Windham to Putnam), Thompson addition (6.6 miles from Thompson to the Massachusetts state line), and an additional 3.6-mile spur to Colchester. Recognized as a national recreation trail by the U.S. Department of the Interior in 2002, it offers scenic routes for hiking and biking. This southern section of the trail near East Hampton is a gravel crushed trail that is great to ride on its own, or to access singeltrack in the nearby Salmon River Forest.

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Enjoy the beauty of the historic Middle Haddam Road Bridge, a captivating stone structure. The Air Line Trail crosses directly over this arch bridge, offering cyclists a scenic view of the area's history and natural surroundings.

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From here you can take the Colchester Spur Trail. The area surrounding the trail played a small but fascinating role in the American Revolution. Look for markers mentioning skirmish sites and troop movements.

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AverieOutside
January 20, 2024, Air Line Trail

The Air Line Trail is a paved 50-mile multi-use trail that connects the cities of Thompson and Portland. This trail is open to walkers, bikes, and even horses.

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Birch Hill Road Open Space West is a nature reserve southeast of Grayville Falls, situated right next to the Air Line State Park Trail. Undeveloped, forested land covers the area between the town's many residential developments, adding to the rural character of this beautiful area.

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This park runs alongside the Willimantic River, providing scenic views of the water. On the opposite side, there are train tracks where you can occasionally observe interesting carts passing by.

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Air Line State Park Trail is a gravel crushed trail that runs on an old rail bed. It's a great trail to ride on its own or to access singeltrack in the Salmon River Forest.

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Loose gravel that is very easy for road bike tires. Very quiet and it dead ends after the trail crosses Depot Hill Road

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Frequently Asked Questions

How many touring cycling routes are available in Portland?

Portland offers a variety of touring cycling routes. According to komoot data, there are 9 routes available, ranging from moderate to difficult, providing diverse options for cyclists.

What is the overall rating for touring cycling routes in Portland?

Touring cycling routes in Portland are highly regarded by the komoot community, boasting an average rating of 5.0 stars from over 17 reviews. Cyclists frequently praise the varied terrain and scenic landscapes.

Are there any circular touring cycling routes in Portland?

Yes, many touring cycling routes in Portland are designed as loops, offering convenient starting and ending points. For example, you can explore the Former Lyman Viaduct – Air Line Trail loop from East Hampton, a challenging 40.1-mile route, or the moderate Former Lyman Viaduct loop from East Hampton, which covers 12.9 miles.

What is the best time of year for touring cycling in Portland?

Portland's temperate climate generally allows for year-round cycling. However, the spring and fall offer particularly pleasant conditions with mild temperatures and beautiful scenery. The Willamette Valley, in particular, is known for its favorable climate for cycling throughout much of the year.

Are there routes suitable for experienced touring cyclists?

Absolutely. Portland and its surroundings offer several challenging routes for experienced touring cyclists. The Former Lyman Viaduct – Air Line Trail loop from East Hampton is classified as difficult, covering over 40 miles with significant elevation changes, providing a robust challenge.

Are there easy touring cycling routes for beginners?

While many routes in the immediate komoot selection are moderate to difficult, Portland's extensive cycling infrastructure includes many easier, flatter paths suitable for beginners. The city's urban greenways and riverfront paths, like sections of the Springwater Corridor or Vera Katz Eastbank Esplanade (mentioned in regional research), offer gentler rides. For a moderate option, consider the Former Lyman Viaduct – Colchester Spur Trail junction loop from East Hampton.

Are there family-friendly touring cycling routes in Portland?

Portland is known for its family-friendly cycling options, especially on its extensive network of bike paths and boulevards. While specific routes in this guide are moderate to difficult, the broader region offers trails like the Springwater Corridor, which is generally flat and paved, making it suitable for families. Always check the route's difficulty and length to ensure it matches your family's abilities.

Are dogs allowed on touring cycling routes in Portland?

Many of Portland's bike trails and parks are dog-friendly, provided dogs are kept on a leash. For example, the Springwater Corridor is generally welcoming to dogs. Always check specific trail regulations before heading out, as rules can vary by location, especially in protected natural areas.

What natural attractions can I see along touring cycling routes near Portland?

Near Portland, you can discover several natural attractions. You might encounter the serene Wadsworth Little Falls, the impressive Giant Laurel, or enjoy views from Higby Cliffs. The region also features the Bradley Hubbard Reservoir and the summit of Lamentation Mountain.

Are there any interesting landmarks or places to explore near the touring cycling routes?

Yes, the area around Portland offers various points of interest. Beyond natural features, you might come across the Mattabesett Trail, a significant hiking trail, or the historic Coginchaug River Dam (Pistol Shop Dam). The broader Portland area is rich with urban parks, gardens, and riverfront areas to explore.

Which routes offer scenic viewpoints?

Many routes in the Portland area provide scenic vistas. The Higby Cliffs offer excellent viewpoints. Regionally, the Columbia River Gorge is renowned for its panoramic views, and urban parks like Mount Tabor and Washington Park also provide stunning cityscapes and natural beauty.

Are there cafes or pubs along the touring cycling routes?

Portland's strong cycling culture means many routes, especially those closer to urban areas or passing through towns, have cafes, pubs, and other amenities nearby. While specific routes in this guide don't detail amenities, popular trails like the Springwater Corridor or those in the Willamette Valley often have convenient stops for refreshments.

Are there accommodation options near the touring cycling routes?

Yes, you'll find various accommodation options near Portland's touring cycling routes, ranging from hotels and B&Bs in towns to campgrounds in more rural settings. Areas like the Willamette Valley, known for its scenic bikeway, offer charming stays in wine country, while the city of Portland provides numerous choices for overnight stays.

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