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10 Best Cycling Routes In Chesapeake, Virginia


by Cecelia Wooley


Chesapeake, Virginia, offers a plethora of scenic and diverse cycling routes that cater to riders of all skill levels. From leisurely rides along the tranquil waterfront to challenging trails through lush woodlands, there's something for every cycling enthusiast to explore. Whether you're a local resident or a visitor seeking an unforgettable cycling experience, Chesapeake's varied terrain and picturesque landscapes provide the perfect backdrop for an exhilarating ride.

In this article, we'll delve into the top 10 cycling routes in Chesapeake, Virginia, each offering its own unique charm and adventure. Whether you're seeking a leisurely family outing or an adrenaline-pumping mountain biking excursion, Chesapeake has a route to suit your preferences. So, grab your helmet, pump up those tires, and get ready to embark on an unforgettable cycling journey through the stunning vistas of Chesapeake, Virginia.

The Dismal Swamp Trail

The Dismal Swamp Trail, a picturesque 8.5-mile route, offers a serene escape into nature. This trail, part of the National Rails-to-Trails Conservancy, winds through lush forests and alongside the historic Dismal Swamp Canal. Cyclists can revel in the tranquility of the surroundings while spotting diverse wildlife, including turtles, birds, and the occasional river otter. The flat, well-maintained surface makes it an ideal choice for cyclists of all skill levels, providing a peaceful and rejuvenating ride.

The Northwest River Park Trail

Nestled within the Northwest River Park, this 7.5-mile trail is a hidden gem for cycling enthusiasts. The scenic path meanders along the tranquil Northwest River, offering breathtaking views and a chance to immerse in the region's natural beauty. Cyclists can relish the shade provided by the towering trees and may even encounter deer and other wildlife along the way. With its gentle terrain and well-marked paths, this route is perfect for a leisurely ride or a family cycling adventure.

The Chesapeake Arboretum Trail

The Chesapeake Arboretum Trail, spanning 3 miles, is a delightful cycling route that winds through a stunning 48-acre wooded oasis. As cyclists pedal through this enchanting landscape, they are treated to a diverse array of flora and fauna, including azaleas, camellias, and magnolias. The tranquil ambiance and well-maintained paths make this trail an idyllic setting for a leisurely bike ride, providing a peaceful retreat from the hustle and bustle of everyday life.

The Battlefield Boulevard Trail

The Battlefield Boulevard Trail, stretching 6 miles, offers cyclists a blend of natural beauty and historical significance. This route traverses through lush greenery and alongside the Great Dismal Swamp, providing a serene backdrop for a scenic ride. Cyclists can also explore the area's rich history, passing by landmarks such as the historic Dismal Swamp Canal and the Civil War-era Dismal Swamp Line. With its combination of natural splendor and historical intrigue, this trail promises a captivating cycling experience.

The Deep Creek Lock Park Trail

The Deep Creek Lock Park Trail, a 3.5-mile route, invites cyclists to embark on a journey through history and nature. This trail follows the historic Dismal Swamp Canal and offers picturesque views of the surrounding woodlands and waterways. Cyclists can also explore the Deep Creek Lock Park, where they can learn about the fascinating history of the canal and its role in shaping the region. With its blend of natural beauty and historical charm, this trail provides a captivating cycling adventure for enthusiasts of all ages.

The Elizabeth River Park Trail

The Elizabeth River Park Trail, spanning 2 miles, offers cyclists a delightful waterfront cycling experience. This scenic route follows the tranquil shores of the Elizabeth River, providing stunning views and a refreshing breeze. Cyclists can revel in the serene ambiance as they pedal along the well-maintained paths, taking in the sights of passing boats and the natural beauty of the riverfront. With its peaceful atmosphere and captivating vistas, this trail is perfect for a relaxing and rejuvenating cycling excursion.

The Oak Grove Lake Park Trail

The Oak Grove Lake Park Trail, a 1.5-mile loop, is a charming cycling route nestled within the scenic Oak Grove Lake Park. Cyclists can enjoy a leisurely ride around the picturesque lake, surrounded by lush greenery and serene natural beauty. The well-maintained trail offers a peaceful escape for cyclists, providing an opportunity to unwind and connect with nature. With its tranquil setting and gentle terrain, this trail is an ideal choice for a casual cycling outing or a peaceful solo ride.

The Great Bridge Lock Park Trail

The Great Bridge Lock Park Trail, spanning 1.5 miles, invites cyclists to explore a historic gem nestled along the Intracoastal Waterway. This scenic route follows the picturesque waterfront, offering captivating views and a glimpse into the area's rich maritime heritage. Cyclists can pedal through the park's serene surroundings, taking in the sights of the historic lock and dam, as well as the tranquil waters of the waterway. With its blend of natural beauty and historical significance, this trail promises a memorable cycling experience.

The South Norfolk Jordan Bridge Trail

The South Norfolk Jordan Bridge Trail, a 5-mile route, provides cyclists with a unique and exhilarating cycling experience. This trail spans the iconic Jordan Bridge, offering stunning panoramic views of the Elizabeth River and the surrounding waterfront. Cyclists can savor the thrill of crossing the bridge and taking in the breathtaking vistas of the river and the city skyline. With its blend of scenic beauty and urban charm, this trail offers an unforgettable cycling adventure for enthusiasts seeking a one-of-a-kind experience.

The Chesapeake Expressway Trail

The Chesapeake Expressway Trail, a 4-mile route, offers cyclists a scenic and convenient cycling option. This trail runs parallel to the Chesapeake Expressway, providing cyclists with a dedicated path for a safe and enjoyable ride. With its smooth surface and well-marked lanes, this route is ideal for cyclists looking for a convenient and accessible cycling experience. Whether for a leisurely ride or a brisk workout, the Chesapeake Expressway Trail offers a versatile and enjoyable cycling opportunity for enthusiasts of all levels.


Exploring the cycling routes in Chesapeake, Virginia, offers a delightful blend of natural beauty, historical charm, and invigorating exercise. From the scenic trails at Northwest River Park to the picturesque landscapes along the Dismal Swamp Canal Trail, cyclists can immerse themselves in the region's diverse terrain and rich heritage. Whether you seek a leisurely ride or a challenging adventure, Chesapeake's cycling routes cater to all skill levels and preferences. With its serene waterways, lush woodlands, and captivating landmarks, Chesapeake beckons cyclists to embark on unforgettable journeys through its captivating landscapes.


Q: Are the cycling routes in Chesapeake suitable for beginners?
A: Yes, Chesapeake offers a variety of cycling routes that cater to beginners, with flat and well-maintained trails such as the Dismal Swamp Canal Trail providing an ideal starting point for novice cyclists.

Q: Are there bike rental options available in Chesapeake?
A: Yes, visitors can access bike rental services at various locations in Chesapeake, making it convenient for travelers to explore the cycling routes without needing to bring their own bicycles.