Walking Paths & Trails
Whether you're a resident or a visitor, our town offers a variety of scenic routes that showcase the natural beauty and charm of Oakland, Maryland. From easy strolls through historic downtown to more immersive nature experiences in our parks, there's something for everyone. Our trails and paths provide opportunities for outdoor recreation, fitness, and relaxation, all while connecting you to Oakland’s vibrant community and picturesque surroundings. Explore what makes Oakland the perfect destination for a walk in the woods or a leisurely stroll by the water.
Oakland Heritage Trail
The Glades Biking/Walking Trail starts at the Oakland Town Parking Lot at the Asa McCain Walking Bridge. It is a one mile, lit path, which passes by the historic Washington Spring on the way to the Glades Town Park. At the Glades Town Park there is another one mile loop. This is a paved trail.
Surface: pavement
Town Parking Lot Trailhead: S 1st Street, Oakland, Maryland, 21550
Glades Park Trailhead: 10 Spruce Lane, Oakland, Maryland 21550
Glades Park Loop Path
The walking path at Glades Park is a paved, one-mile loop that circles the park, offering a smooth and scenic route for all ages. The Oakland Heritage Trail ends at the Glades Park Loop so you can easily start at the Town Parking lot. As you follow the path, you'll enjoy views of the park’s pond, playground, and recreational courts, making it a perfect spot for a leisurely stroll or light exercise. Add to your workout on the outdoor exercise equipment along the path.
Surface: pavement
Glades Park Trailhead: 10 Spruce Lane, Oakland, Maryland, 21550
88 Bridge Trail
The 88 Bridge Trail is located on Liberty Street. The trailhead is connected to the Glades Park Loop Path. It is 7/10 of a mile long each way. The trail takes you from the Glades Park to the site of the 88 Bridge and Civil War blockhouses. The trail is lined with five historical markers explaining the role of the B&O Railroad in Garrett County and the Civil War.
Surface: gravel
Glades Park Trailhead: 10 Spruce Lane, Oakland, Maryland, 21550
Fort Alice Trailhead: Liberty Street, Oakland, Maryland, 21550 (no parking - park at Glades Park)
Broadford Park Trail System
Inside Broadford Park you’ll find an extensive trail system ready for walking, running, mountain biking, cross country skiing, and snowshoeing. The trail system provides a single track experience with a decreased barrier for entry to trail users seeking a beginner to intermediate level trail experience while providing room for progressive development of skills. The trail system was primarily designed with modern mountain bike use in mind, taking care to embrace a flowing trail experience through thoughtful design, curvilinear alignments, gradual changes in trail user speed, technical trail features, alternative line choices, and construction techniques such as tread in-sloping, rollers, brollers, and bermed turns.
123 Recreation Lane, Mountain Lake Park, Maryland 21550
Trailheads available at both parking lots