5.0
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256
runners
51
runs
Jogging around Oakland offers diverse landscapes, from urban waterfront paths to challenging hilly trails. The region features a variety of terrains, including paved loops around urban lakes, wooded paths through redwood forests, and coastal routes along the estuary. Elevations range from flat, accessible paths to more demanding climbs in the hills, providing options for different fitness levels.
Last updated: June 23, 2026
18
runners
20.1km
02:04
50m
50m
The Gravois Greenway, also known as Grant's Trail, offers a unique jogging experience through St. Louis County, blending natural beauty with historical significance. You'll traverse a smooth, paved multi-use path that follows a historic railroad line, winding through pine and oak forests, past striking old rock cuts, and even a restored wetland area. Keep an eye out for Clydesdale horses near Grant's Farm as you enjoy the varied scenery on this predominantly flat route.
This 12.5-mile (20.1 km) route is rated difficult primarily due to its length, not technical challenge, with a gentle 170 feet (52 metres) of elevation gain. It takes approximately 2 hours and 4 minutes to complete, making it ideal for those seeking a sustained, accessible run. Trailheads along the route, such as Union Road Country Park, provide convenient parking and amenities, ensuring a comfortable visit.
As an integral part of the larger Great Rivers Greenway system, this trail connects seamlessly with the River des Peres Greenway, forming an extensive network. It provides easy access to significant local attractions like the U.S. Grant National Historic Site and Officer Blake C. Snyder Memorial Park, offering more than just a run. The consistent surface and diverse points of interest make it a fantastic option for family jogging or anyone looking for a long, engaging outing.
1
runners
4.87km
00:30
40m
40m
Enjoy an easy 3.0-mile (4.9 km) jogging route through Kirkwood Park, featuring paved paths, a clear lake, and forested hills.

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15
runners
8.42km
00:52
30m
30m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
7
runners
13.6km
01:25
90m
90m
The Kirkwood loop from Webster Groves offers a refreshing blend of urban green spaces and natural settings, perfect for a varied jogging experience. You'll find yourself moving between paved paths and unpaved sections, winding through lush oak-hickory forests and along river greenways. Highlights include the serene Walker Lake in Kirkwood Park and the distinctive old rock cuts and native wildflowers along the Gravois Greenway, providing a constantly changing backdrop for your run.
Planning your visit is straightforward, as these popular jogging routes in Kirkwood and Webster Groves are well-connected and easily accessible. You can often find convenient parking in either community, with Kirkwood's train station area being a great starting point, offering nearby cafes for a quick coffee before or after your workout. The route is generally suitable for all seasons, though spring and fall offer particularly pleasant temperatures.
What makes this route stand out is the seamless integration of natural beauty with the local charm of both Kirkwood and Webster Groves. You'll pass by historic architecture and vibrant community areas, making it more than just a run; it's an exploration of these distinct Missouri towns. This moderate 8.4-mile (13.5 km) loop, with 306 feet (93 metres) of elevation gain and an estimated duration of 1 hour and 24 minutes, is ideal for those seeking a rewarding and accessible jogging adventure.
8
runners
5.90km
00:37
50m
50m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Oakland
Grant's Trail is a flat and relaxed 12-mile trail that is easily accessible from downtown St Louis. It's the perfect running trail that passes a number of green parks.
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This is a lovely park along Grant's Trail with the Gravois Creek flowing right through it. You can jump off the pathway and into the park and catch your breath on the grassy patch next to the water.
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Kirkwood is a wonderful place to begin or end a run. It has a local train station, nearby park and a number of great cafés including Kaldi's Coffee and The Pioneer Bakery Café.
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This is a gem of a park in the Kirkwood area that is perfect for running. It features a fully paved pathway, lake, shelters, amphitheatre and beautiful scenery.
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This national historic site marks where General (and later President) Ulysses S. Grant met his future wife, and where they lived for some time. Although Grant is known as the general who led the Union Army to victory in the US Civil War, it's important to recognize that he held a workforce of slaves here for some time. You can learn more about this national historic site here: https://www.nps.gov/ulsg/index.htm
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Oakland offers a diverse selection of running routes. On komoot, you can find over 40 routes, ranging from easy urban loops to more challenging trails through the hills and redwood forests. This variety ensures options for all fitness levels and preferences.
Yes, Oakland has several easy and relatively flat options. The Lake Merritt Loop is a popular choice, offering a nearly flat, 3.4-mile paved path around the urban estuary. Another accessible option is the 2.5-mile stretch of the San Francisco Bay Trail along the Oakland Estuary, from Jack London Square to Union Point Park.
For those seeking a challenge, Oakland's hills provide excellent opportunities. Redwood Regional Park and Joaquin Miller Park both feature trails with varying elevations, allowing runners to experience the tranquility of deep nature away from the city's hustle and bustle. The East Bay Skyline National Recreation Trail also offers diverse terrain and expansive views over its 7.1-mile course.
Oakland boasts many scenic routes. The Lake Merritt Loop offers views of the lake, Children's Fairyland, and the Lakeside Park Garden Center. For panoramic vistas, the East Ridge Overlook within Redwood Regional Park is exceptional. The San Francisco Bay Trail along the Estuary provides views of the classic cranes at the port and the San Francisco skyline, while the Oyster Bay Loop offers beautiful Bay views.
Many of Oakland's parks and green spaces are dog-friendly, making it a great place to run with your canine companion. Areas like Redwood Regional Park and Joaquin Miller Park typically allow dogs on trails, though it's always best to check specific park regulations regarding leashes and restricted areas before you go.
Absolutely. The Lake Merritt Loop is an excellent family-friendly option due to its flat, paved surface and scenic urban environment. Many of Oakland's numerous city parks also offer well-maintained paths suitable for families, often with amenities like picnic spots and playgrounds nearby.
Oakland's running routes showcase a variety of natural features and landmarks. You can encounter the urban estuary of Lake Merritt, majestic redwood forests in Redwood Regional Park, and volcanic formations at Sibley Volcanic Regional Preserve, which also features a labyrinth. Along the waterfront, you'll see the San Francisco Bay and the city skyline.
Yes, Oakland has several excellent loop routes. The most prominent is the 3.4-mile Lake Merritt Loop, a popular circular path around the urban lake. The 3.9-mile Oyster Bay Loop in Oyster Bay Regional Shoreline also offers a moderate circular route with Bay views and diverse wildlife.
The komoot community highly rates the running experience in Oakland, with an average score of 5.0 stars. Runners often praise the incredible variety of terrain, from serene redwood forests to vibrant urban waterfronts, and the stunning views available throughout the city's diverse parks and trails. More than 290 runners have used komoot to explore Oakland's varied terrain.
Yes, Oakland is a hub for running events. The Lake Merritt Loop serves as a central point for several running festivals, including the Oakland Running Festival and the Oaktown Half Marathon, attracting runners from across the region.
Many of Oakland's popular running spots are well-served by public transport. The Lake Merritt Loop, for instance, is centrally located and easily accessible by BART and local bus routes. Other parks like Redwood Regional Park and Joaquin Miller Park may require a combination of public transport and a short walk or ride to reach trailheads.
Beyond the trails, Oakland offers many attractions. You can explore places like the River des Peres Greenway, the Meramec Greenway Trail – Eastern Section, or visit the Laumeier Sculpture Garden. For more general information on things to do in the city, you might find resources like Visit Oakland's guide to 100 things to do helpful.


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