4.8
(25)
469
hikers
42
hikes
Hiking around Twin Oaks offers access to several local and regional parks, including Castlewood State Park and the Forest 44 Conservation Area. The area is characterized by forested trails, paths along the Meramec River, and routes suitable for a range of fitness levels. These hikes near Twin Oaks provide a mix of easy riverside walks and more moderate woodland loops.
Last updated: June 25, 2026
5.0
(2)
7
hikers
2.90km
00:44
0m
0m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
2.18km
00:33
10m
10m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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4.3
(6)
67
hikers
5.51km
01:27
50m
50m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
5.0
(2)
34
hikers
2.93km
00:48
50m
50m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
4.8
(5)
30
hikers
7.14km
01:55
90m
90m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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Lone Wolf Trail is a fun woodland trail in Castlewood State Park. Parts of the path can be rocky and rooty underfoot, so be mindful where you step. There are some wonderful views on offer across the Meramec River from parts of the trail.
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Simpson Park Lake is a refreshing oasis in the Valley Park area that offers a perfect location for a run. It features a fully paved, multi-use trail that runs on the southern edge of the lake and has parking areas, picnic shelters and is a stones throw away from the Meramec River.
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Henry L. Simpson Park, also known as Simpson Park, is a 148-acre park with a 78-acre lake. This park has paved multi-use trails, a playground, picnic shelters, and sports fields.
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The Lone Wolf Trail is right in the heart of Castlewood State Park. The trail shares a path with the Riverscene Trail very briefly near an observation deck and also offers some views of its own along the path. The loop has a number of trail intersections with other paths in the park, but they are mostly well-marked and easy to follow.
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The Grotpeter Trail is the most northern trail in the Castlewood State Park trail system. The twists and turns remind you of why so many mountain bikers love these trails, but they are perfect for a forest hike as well. The trails are pretty well-marked in this part of the park, and you'll have several options to branch off of this main trail onto some of the other shorter trails in the area.
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The Riverscene Trail is the most popular trail in Castlewood State Park. The trail passes through a forest scene, a wide open are next to a beach area, and along the banks of a shaded river. The variety of scenery with pretty smooth terrain makes this loop trail a perfect choice for a lot of different occasions.
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Yes, dogs are generally welcome in the parks and conservation areas near Twin Oaks, including Castlewood State Park and Forest 44 Conservation Area. However, they must be kept on a leash at all times. Always be sure to clean up after your pet to help keep the trails enjoyable for everyone.
Absolutely. The region has many gentle trails perfect for a family outing. For a shorter, manageable walk, consider the Lone Wolf Trail loop — Castlewood State Park. It's an easy path of less than 2 miles, making it a great choice for hikers of all ages and fitness levels.
Most of the popular hiking areas, such as Castlewood State Park and Forest 44 Conservation Area, have designated parking lots near the main trailheads. These can fill up quickly, especially on weekends and holidays, so arriving earlier in the day is recommended to secure a spot.
Spring and autumn are ideal for hiking around Twin Oaks. During these seasons, the weather is pleasantly mild and the forests are at their most scenic, with spring wildflowers or vibrant fall foliage. Summer can be hot and humid, so if you hike then, be sure to start early and bring plenty of water.
Yes, many of the trails in the area are loops, which allow you to enjoy a varied hike without retracing your steps. The region features over 20 easy loop trails and several moderate ones, offering plenty of options for a continuous journey through the local parks and woodlands.
The parks and conservation areas around Twin Oaks are home to a variety of wildlife. It's common to see white-tailed deer, squirrels, and a wide array of bird species. Near the Meramec River, you might also spot turtles, herons, and other waterfowl. Keep a respectful distance from any animals you encounter.
Yes, for those seeking more of a challenge, there are moderately difficult trails available. The Chubb Trail — Castlewood State Park offers a longer route of nearly 5 miles with some elevation changes, providing a good workout through the forested landscape.
The area is highly rated by the komoot community. Reviewers often praise the well-maintained trails, the beautiful scenery along the Meramec River, and the peaceful atmosphere of the woodlands. The accessibility of the parks from the city is also a frequently mentioned highlight.
Yes, some of the multi-use trails in the region are open to horseback riding. The Forest 44 Conservation Area, for example, has wider trails that are popular with equestrians. Always check the specific park regulations to confirm which trails are designated for horse use.
For a day hike, it's essential to wear sturdy, comfortable footwear. We recommend bringing plenty of water, especially in warmer months, along with some snacks. It's also wise to pack a small first-aid kit, sun protection like a hat and sunscreen, and insect repellent.
You can explore over 25 different hiking routes around Twin Oaks. The selection includes 21 easy trails perfect for casual walks and 7 moderate routes for those looking for a bit more of a challenge, ensuring there's a path for every type of hiker.


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