5.0
(1)
49
hikers
17
hikes
Hiking around Lakeside Woods offers diverse terrain within a 140-acre wilderness area characterized by wooded and rugged hill country. Trails provide scenic views of Lake Taneycomo and wind along bluffs. The region features a mix of natural elements, including wetlands near the lake and varied elevations.
Last updated: June 28, 2026
6
hikers
6.55km
02:01
200m
240m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
2
hikers
6.92km
02:06
220m
230m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

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1
hikers
5.87km
01:37
100m
90m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
1
hikers
2.79km
00:46
50m
50m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
1
hikers
3.84km
01:05
80m
80m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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Lakeside Woods offers a diverse landscape of 140 acres, featuring wooded and rugged hill country. You'll find trails winding along bluffs, providing scenic views of Lake Taneycomo. The area also boasts unique natural elements like wetlands near the lake, and some trails may lead you past a waterfall, caves, and grottoes, though the waterfall's flow can depend on recent rainfall.
Yes, Lakeside Woods provides a variety of trails catering to different fitness levels. The area has 15 hiking routes in total, with 8 classified as easy, 5 as moderate, and 2 as difficult. For an accessible path through natural surroundings, consider the easy Cranberry Mountain Trail.
Hikers can explore several interesting historical and man-made features. Along the Bluff Trail, you'll find the site of the historic Owen Homestead, dating back to 1911. A significant attraction is a set of 315 man-made stone steps, laid between 1937 and 1938, that lead down towards Lake Taneycomo. The property also features almost 2,000 feet of hand-built stone walls, showcasing historical craftsmanship.
Many trails offer glimpses of Lake Taneycomo, but for particularly stunning vistas, look for points along the bluffs. There are also covered pavilions with stone columns that serve as picnic areas with beautiful lake views. Specifically, an overlook at the farthest point south of the Ridge Trail is known for providing excellent lake views.
Yes, Lakeside Woods features several circular routes. A popular option is the Pootatuck State Forest Loop, a moderate 4.1-mile trail that navigates through varied forest landscapes. Another well-liked circular path is the Pine Hill to Squantz Pond Loop, which is 4.3 miles long and leads through wooded areas.
The hiking routes in Lakeside Woods are highly regarded by the komoot community, holding an average score of 5.0 stars from 1 review. Over 50 hikers have used komoot to explore the varied terrain, often praising the diverse landscapes and well-maintained paths that offer a refreshing escape.
Yes, Lakeside Woods is considered family-friendly. Near the entrance, you'll find a nature playground and a pavilion, perfect for younger visitors. Many of the 8 easy trails are suitable for families, such as the Lillinonah Loop, which is a shorter, easy hike.
While specific parking details for each trailhead are best checked on individual route pages, Lakeside Forest Wilderness Area generally provides parking facilities for visitors accessing its extensive trail system. It's advisable to check local signage upon arrival for designated parking areas.
Beyond the trails themselves, there are several points of interest in the vicinity. You can visit Squantz Pond State Park or enjoy the serene waters of Squantz Pond. For more natural beauty, Harrybrooke Park offers additional forest exploration.
Lakeside Forest Wilderness Area is generally dog-friendly, allowing leashed dogs on its trails. It's always a good idea to check for any specific signage at the trailhead regarding pet regulations, but in general, your canine companion can join you on your hike.
Lakeside Forest Wilderness Area boasts an extensive trail system, offering a total of 5.3 miles (approximately 8.5 kilometers) of hiking trails for visitors to explore. These trails are spread across the 140-acre wilderness area, providing ample opportunities for outdoor activity.
Yes, for those seeking a more strenuous experience, Lakeside Woods offers a couple of difficult routes. While specific names for these difficult trails are not detailed here, the overall network includes options with significant elevation changes and rugged terrain to challenge experienced hikers. For a moderate challenge, consider the Pootatuck State Forest Loop with its varied forest landscapes and elevation changes.


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