Cycling Dreams: Touring America on Two Wheels

Explore iconic landscapes and cities on two wheels with our guide to 15 top cycling destinations. From Portland, Maine’s tranquil shores to Portland, Oregon’s bustling bike lanes, find the best routes, travel tips, and more for all skill levels. Enjoy eco-friendly adventures and navigate America’s diverse trails and urban paths with ease.

1. Portland, Oregon 

Portland is often hailed as one of the most bike-friendly cities in the United States, with over 350 miles of bikeways and a vibrant cycling culture. The city’s comprehensive network of bike lanes and paths allows cyclists to easily explore its diverse neighborhoods, scenic parks, and bustling downtown areas. A popular route is the Springwater Corridor, a paved trail that stretches from the city’s waterfront through various neighborhoods and into the surrounding natural landscapes. Riders can enjoy stops at artisan coffee shops, local breweries, and public art installations along the way. 

Insider’s Tip: Explore the Eastbank Esplanade for stunning views of the city skyline and Mount Hood, which are especially beautiful at sunset. 

When to Travel: May through October offers the driest weather and most pleasant temperatures for cycling. 

How to Get There: Fly into Portland International Airport and utilize the city’s bike-share program, Biketown, to start your adventure right from the airport.

2. San Francisco, California 

Known for its iconic hills and stunning vistas, San Francisco offers a challenging yet rewarding cycling experience. The city’s bike routes provide breathtaking views of the Golden Gate Bridge, Alcatraz, and the Pacific Ocean. Cyclists can ride along the Embarcadero, climb the slopes of Twin Peaks, or venture across the Golden Gate Bridge to Sausalito for a picturesque day trip. The diverse terrain caters to various skill levels, from leisurely rides along the waterfront to more strenuous climbs. 

Insider’s Tip: For a unique experience, bike the 49-mile Scenic Drive at a leisurely pace to explore major landmarks and hidden gems. 

When to Travel: September to November, when the weather is warmest and fog is minimal, making for ideal cycling conditions. 

How to Get There: San Francisco International Airport is the primary gateway, with excellent public transit connections to the city and numerous bike rental and tour options.

3. Minneapolis, Minnesota 

Minneapolis is renowned for its extensive cycling infrastructure and the famous Chain of Lakes, a series of parks and water bodies linked by well-maintained bike trails. The city’s dedicated bike lanes and paths, such as those around Lake Harriet and Lake Calhoun, offer scenic urban rides with a blend of natural beauty. The Midtown Greenway, a rail trail through the heart of Minneapolis, provides a fast, safe, and scenic means of east-west travel. 

Insider’s Tip: Don’t miss the chance to ride the Cedar Lake Trail, known locally as “America’s first bike freeway,” for its smooth, wide paths and commuter-friendly design. 

When to Travel: Late spring to early fall, when temperatures are mild and the city’s flora is in full bloom. 

How to Get There: Fly into Minneapolis-St. Paul International Airport offers nearby bike rental facilities to get you quickly onto the city’s trails.

4. Boulder, Colorado 

Boulder offers a unique cycling experience with its dramatic mountain scenery and a strong community of cyclists. The city features a variety of trails that cater to different cycling disciplines, from road biking along the scenic Boulder Creek Path to mountain biking on the challenging trails of the Flatirons. The city’s commitment to sustainable travel and outdoor recreation is evident in its well-maintained paths and bike-friendly public amenities. 

Insider’s Tip: Explore the Valmont Bike Park, a 42-acre terrain park built specifically for riders of all levels, offering everything from large jumps to kid-friendly circuits. 

When to Travel: Late spring through early autumn for the best weather, avoiding the snowy months when many trails may be less accessible. 

How to Get There: Denver International Airport is the closest major airport, with Boulder just a 45-minute drive away. Shuttle services and public transit options allow easy access to Boulder and its bike trails.

5. Asheville, North Carolina 

Nestled in the Blue Ridge Mountains, Asheville is a haven for cyclists looking for challenging mountain trails and scenic road routes. The Blue Ridge Parkway, known for its breathtaking views and rigorous paths, is a must-ride for serious cyclists. Asheville also boasts a thriving arts community, providing an eclectic mix of cultural stops along its urban routes. 

Insider’s Tip: After a day of cycling, visit the River Arts District to unwind and enjoy local art, live music, and craft beer. 

When to Travel: Spring and fall are ideal, offering cooler temperatures and vibrant foliage without the heavy tourist traffic of summer. 

How to Get There: Asheville Regional Airport offers convenient access, with bike rentals in the city to explore urban and mountain trails.

6. Tucson, Arizona 

Tucson is rapidly becoming a top destination for cyclists due to its year-round biking weather and extensive bike lanes and trails network. The city is surrounded by five mountain ranges, providing ample opportunities for mountain biking, while the urban Tucson Loop offers over 130 miles of paved paths connecting parks, restaurants, and other attractions. Tucson’s geography offers a unique blend of desert landscapes, complete with cacti and stunning sunsets, making for picturesque rides. 

Insider’s Tip: For an unforgettable experience, plan a ride during the early morning or late afternoon to capture the breathtaking Arizona sunrises and sunsets illuminating the desert. 

When to Travel: Late fall through early spring to avoid the extreme heat of the summer months. 

How to Get There: Fly into Tucson International Airport, where bike rentals are readily available to take advantage of the extensive trail network right from arrival.

7. Austin, Texas 

Known for its vibrant music scene and outdoor culture, Austin offers cyclists a dynamic environment to explore on two wheels. The city boasts several scenic trails that run through urban areas and along bodies of water, such as the Lady Bird Lake Hike-and-Bike Trail, which offers downtown views coupled with natural tranquility. Austin’s bike-friendly initiatives and active community make it an ideal place for cycling enthusiasts to immerse themselves in the local culture. 

Insider’s Tip: Join one of the many group rides organized by local biking communities to get a local’s perspective on the best routes and post-ride hangouts. 

When to Travel: Spring and fall provide the best weather conditions for cycling, with mild temperatures and minimal rainfall. 

How to Get There: Austin-Bergstrom International Airport serves as the gateway to the city, with various transportation options available to take you and your bike downtown or to your chosen trail.

8. Madison, Wisconsin Overview: 

Madison’s reputation as a premier biking city is well-deserved, thanks to its dedicated community of cyclists and a well-established network of biking trails. The city offers routes that cater to leisurely rides around lakes and more ambitious trails through rolling hills. Key routes include the Capital City State Trail and the Lake Monona Circuit, offering scenic views and well-maintained paths. 

Insider’s Tip: Visit during the late summer to participate in the annual Ride the Drive event, when the city closes its major streets to car traffic, allowing cyclists to take over. 

When to Travel: Late spring to early fall to enjoy the lush greenery and comfortable cycling weather. 

How to Get There: Dane County Regional Airport is just a few miles from downtown Madison, with bike rentals available to explore the city’s extensive bikeways upon arrival.

9. Philadelphia, Pennsylvania 

Philadelphia’s extensive multi-use trail systems, such as the Schuylkill River Trail and the Wissahickon Valley Park trails, provide urban and rustic cycling experiences enveloped in rich American history. Its expanding bike lanes and community biking events show the city’s commitment to becoming more bike-friendly. Cycling in Philadelphia offers a healthy way to explore the city and unique views of historic sites and the downtown skyline. 

Insider’s Tip: Don’t miss a ride through the historic district, where you can see iconic landmarks like the Liberty Bell and Independence Hall from your bike. 

When to Travel: Spring and autumn are the best times to visit, offering cooler temperatures and colorful foliage. 

How to Get There: Philadelphia International Airport is centrally located, and the city’s bike share program, Indego, offers convenient bike rentals at stations throughout the city.

10. Seattle, Washington 

Seattle’s cycling scene is as vibrant as its coffee culture, with bike paths showcasing the city’s natural beauty and urban sophistication. Trails like the Burke-Gilman Trail or the Alki Trail in West Seattle offer panoramic views of the mountains and Puget Sound. The city’s hilly terrain provides a good challenge for more experienced cyclists, while flat trails around the lakes cater to more casual riders. 

Insider’s Tip: For a unique Seattle cycling experience, ride the ferry to Bainbridge Island and enjoy a scenic 35-mile loop that offers stunning views back to the city. 

When to Travel: Summer offers the driest weather, making it the ideal time for cycling. 

How to Get There: Seattle-Tacoma International Airport is the main entry point, with downtown Seattle just a short drive or bus ride away, where numerous bike shops offer rentals.

11. Denver, Colorado 

Denver is a city where urban sophistication meets outdoor adventure, making it an ideal destination for cyclists. The city’s extensive network of bike lanes and trails, such as the Cherry Creek Trail and the South Platte River Trail, provide access to Denver’s diverse neighborhoods and beautiful natural surroundings. These trails connect riders to key attractions like the Denver Art Museum, Red Rocks Amphitheater, and the Rocky Mountain Arsenal National Wildlife Refuge, offering both cultural experiences and natural escapes. 

Insider’s Tip: Take the time to explore the Denver Beer Trail by bike. It’s a fun way to sample what the city’s booming craft brewery scene offers, with several breweries conveniently located along its bike paths. 

When to Travel: The best times to cycle in Denver are late spring and early fall when the weather is mild and the scenery peaks with blooming or autumnal colors. 

How to Get There: Denver International Airport is a major hub with excellent public transit connections to downtown, where you can easily rent a bike and start exploring right away.

12. Miami, Florida 

Miami offers cyclists a vibrant, scenic backdrop for rides along the city’s famous beaches and lively urban areas. Routes like the Rickenbacker Causeway provide stunning ocean views and lead to popular spots such as Virginia Key and Key Biscayne, perfect for a leisurely day of cycling and beach activities. Miami’s flat terrain makes it accessible for all levels of cyclists, and the city’s growing network of bike lanes enhances safety and convenience. 

Insider’s Tip: For a truly scenic ride, start early in the morning to catch the sunrise over the Atlantic Ocean as you cycle along Miami Beach’s Ocean Drive, experiencing the area’s iconic architecture and sea breezes without the usual crowds. 

When to Travel: Winter and early spring offer cooler temperatures and lower humidity for comfortable cycling conditions. 

How to Get There: Miami International Airport serves as the primary gateway to the area, with numerous bike rental locations available across the city for visitors.

13. Asheville, North Carolina 

Nestled in the Blue Ridge Mountains, Asheville provides a picturesque setting for cyclists looking for urban and mountain biking experiences. The city is known for its artistic vibe and historic architecture, which can be enjoyed along various bike-friendly routes downtown. More adventurous riders can tackle the trails in the surrounding mountains, which offer challenging climbs and rewarding views of the Appalachian landscape. 

Insider’s Tip: Don’t miss the opportunity to ride the Blue Ridge Parkway. Start at the nearest access point in Asheville and enjoy a section of this famous route known for its sweeping mountain vistas and lush forestry. 

When to Travel: Late spring to early fall is the best time to visit, with cooler temperatures and the natural beauty of the mountains fully accessible. 

How to Get There: Asheville Regional Airport is just a short drive from the city, with bike rentals available to take you straight onto the city’s streets or mountain trails.

14. Portland, Maine 

Portland offers a charming New England cycling experience with its historic waterfront and lighthouse views. The city’s manageable size makes it perfect for bike exploration, with trails and dedicated bike lanes providing safe and scenic routes along the coast and through downtown. Popular rides include the Eastern Promenade for ocean views and the Back Cove Trail for a more tranquil, natural setting. 

Insider’s Tip: Extend your ride to the nearby islands like Peaks Island, which you can reach via a short ferry ride with your bike. The island offers quiet roads perfect for cycling and picturesque views back to the mainland. 

When to Travel: Summer and early fall are the best times to visit when the weather is warm and the coastal views are most inviting. 

How to Get There: Portland International Jetport is conveniently located, with bike rentals available in the city to start your coastal New England adventure.

15. Sedona, Arizona 

Sedona’s stunning red rock landscapes provide a dramatic backdrop for one of the most unforgettable cycling experiences in the U.S. The area’s extensive network of trails caters to mountain bikers with routes ranging from easy rides around the city to challenging technical trails in the canyons. Sedona is a haven for adventure seekers and a place of spiritual significance, which adds an enriching layer to the cycling experience. 

Insider’s Tip: Try the Bell Rock Pathway for a leisurely ride with incredible views of Bell Rock and Courthouse Butte, some of Sedona’s most famous landmarks. 

When to Travel: Spring and fall are ideal, offering cooler temperatures and vibrant colors in the desert landscape. 

How to Get There: Fly into Phoenix Sky Harbor International Airport for approximately two hours to Sedona. Bike rentals and tour services are abundantly available in town, catering to all experience levels.

The Bottom Line

From the tranquil ocean views of Portland, Maine, to the rugged desert trails of Sedona, Arizona, cycling through these destinations offers a unique way to connect with nature and culture across America. Each location presents an opportunity to embrace the outdoors while practicing eco-friendly travel. So gear up and set off on your next cycling adventure, knowing that each pedal brings personal fulfillment and a deeper appreciation of the diverse American landscape.

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Featured Image Credit: Shutterstock / Lissandra Melo.

For transparency, this content was partly developed with AI assistance and carefully curated by an experienced editor to be informative and ensure accuracy.

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