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11 Best Cycling Routes In Portsmouth, Virginia


by Latia Spooner


Portsmouth, Virginia, is a city steeped in history and natural beauty, making it an ideal destination for cycling enthusiasts. With its picturesque waterfront, charming neighborhoods, and well-maintained trails, Portsmouth offers a diverse range of cycling routes that cater to riders of all skill levels. Whether you're a leisurely rider seeking scenic views or a seasoned cyclist looking for a challenging workout, Portsmouth has something to offer.

In this article, we'll explore the 11 best cycling routes in Portsmouth, Virginia, each offering its own unique blend of sights and experiences. From the tranquil paths along the Elizabeth River to the exhilarating trails through lush parks, these routes showcase the city's rich tapestry of landscapes and attractions. So, grab your helmet, pump up those tires, and get ready to embark on a cycling adventure through the heart of Portsmouth.

The Elizabeth River Trail

The Elizabeth River Trail is a scenic 10.5-mile route that winds along the beautiful Elizabeth River, offering cyclists breathtaking views of the water and the city skyline. This popular trail spans from Harbor Park to the Norfolk Naval Shipyard, providing a delightful mix of urban and natural landscapes. Cyclists can enjoy the tranquility of the waterfront, pass by historic sites, and revel in the vibrant atmosphere of the nearby neighborhoods.

The Cannonball Trail

Named after the historic Civil War cannonballs that were manufactured in the area, the Cannonball Trail is a 4.8-mile route that showcases the rich heritage of Portsmouth. Cyclists can explore the city's storied past as they pedal through historic districts, passing by landmarks such as the Hill House and Trinity Church. This route offers a captivating journey through time, allowing riders to immerse themselves in the charm and history of Portsmouth.

The Seawall Trail

The Seawall Trail is a picturesque 3.2-mile route that runs along the waterfront, treating cyclists to stunning views of the river and the Portsmouth Harbor. This scenic pathway is perfect for leisurely rides, providing a serene escape from the hustle and bustle of the city. Cyclists can savor the refreshing sea breeze and admire the maritime beauty while pedaling along this captivating trail.

The Victory Trail

The Victory Trail, spanning 5.3 miles, offers cyclists a delightful blend of natural splendor and historical intrigue. This route takes riders through lush greenery and serene landscapes, providing a peaceful retreat from urban life. Along the way, cyclists can discover significant historical sites, including the Afton Square and Victory Boulevard, making it a compelling journey for history enthusiasts and nature lovers alike.

The Olde Towne Loop

The Olde Towne Loop, a 3.5-mile route, invites cyclists to immerse themselves in the timeless allure of Portsmouth's historic district. This captivating trail winds through cobblestone streets and past well-preserved colonial architecture, offering riders a glimpse into the city's rich heritage. Cyclists can explore quaint shops, charming cafes, and iconic landmarks, making this route a perfect blend of history, culture, and leisurely cycling.

The Churchland Trail

The Churchland Trail, extending 4.2 miles, provides cyclists with a serene and picturesque journey through lush woodlands and tranquil neighborhoods. This route offers a peaceful escape into nature, allowing riders to revel in the beauty of the local flora and fauna. Cyclists can enjoy the refreshing ambiance of the outdoors while pedaling through this scenic trail, making it an ideal choice for those seeking a tranquil and rejuvenating cycling experience.

The Bide-A-Wee Golf Course Trail

The Bide-A-Wee Golf Course Trail, a 2.6-mile route, offers cyclists a unique and refreshing cycling experience amidst the stunning greenery of the golf course. This scenic trail provides a tranquil and leisurely ride, allowing cyclists to enjoy the lush surroundings and the soothing ambiance of the golf course. With its serene atmosphere and picturesque landscapes, this route is perfect for cyclists looking to combine their love for golf and cycling.

The City Park Trail

The City Park Trail, spanning 1.8 miles, is a delightful route that takes cyclists through the scenic City Park, offering a serene and refreshing cycling experience. Riders can pedal through lush green spaces, past tranquil ponds, and under the canopy of majestic trees, immersing themselves in the natural beauty of the park. This route provides a peaceful and rejuvenating cycling adventure, making it an ideal choice for nature enthusiasts and leisure riders.

The Western Branch Trail

The Western Branch Trail, extending 3.7 miles, offers cyclists a tranquil and scenic journey through the serene landscapes of Western Branch. This route takes riders through peaceful neighborhoods and verdant surroundings, providing a refreshing escape into nature. Cyclists can enjoy the calming ambiance of the trail as they pedal through picturesque scenery, making it a perfect choice for those seeking a relaxing and rejuvenating cycling experience.

The Paradise Creek Nature Park Trail

The Paradise Creek Nature Park Trail, a 2.8-mile route, invites cyclists to explore the natural wonders of the Paradise Creek Nature Park. This scenic trail offers riders a captivating journey through lush wetlands, serene forests, and picturesque waterfront views. Cyclists can immerse themselves in the beauty of the park, encountering diverse wildlife and enjoying the tranquility of the natural surroundings, making it an ideal choice for nature lovers and outdoor enthusiasts.

The Craney Island Eastward Trail

The Craney Island Eastward Trail, spanning 4.5 miles, provides cyclists with a unique and captivating journey along the eastern edge of Craney Island. This scenic route offers stunning views of the Elizabeth River and the surrounding marshlands, allowing riders to immerse themselves in the natural splendor of the area. Cyclists can savor the tranquility of the waterfront and the breathtaking vistas, making this trail a perfect choice for those seeking a memorable and picturesque cycling adventure.


Exploring the cycling routes in Portsmouth, Virginia, offers a delightful blend of scenic beauty, historical significance, and recreational opportunities. Whether you're a casual rider or a seasoned cyclist seeking a new adventure, Portsmouth's diverse trails cater to all preferences. From the picturesque Elizabeth River Trail to the tranquil ambiance of City Park, each route presents a unique experience that showcases the city's charm. As you pedal through these paths, you'll encounter a tapestry of natural landscapes, architectural marvels, and cultural landmarks, immersing yourself in the rich tapestry of Portsmouth's heritage. With its well-maintained trails and captivating vistas, Portsmouth stands as a haven for cyclists, beckoning enthusiasts to savor the joy of exploration and discovery on two wheels.


Q: Are the cycling routes in Portsmouth suitable for riders of all skill levels?
A: Yes, Portsmouth offers a variety of cycling routes that cater to riders of different skill levels, from beginners to experienced cyclists. Whether you prefer leisurely rides or more challenging trails, there are options available to suit your abilities.

Q: Are there any bike rental facilities near the cycling routes in Portsmouth?
A: Yes, there are bike rental facilities conveniently located near the cycling routes in Portsmouth. Visitors can easily access rental services to explore the city's scenic trails without needing to bring their own bicycles.