The best walks and hikes around Sleepy Hollow

Embark on the Terra Linda Ridge and 680 Trail for a moderate hike spanning 5.5 miles (8.9 km). You will ascend 893 feet (272 metres) over approximately 2 hours and 35 minutes. The route offers a mix of wide fire roads and narrower singletrack paths, often featuring steep sections that challenge you. As you climb, you will discover expansive views of Marin County, with Mount Tamalpais visible in the distance and Lucas Valley stretching out below. On clear days, you might even catch a glimpse of San Pablo Bay. The trail's character shifts with the seasons, from vibrant spring wildflowers to the welcome shade of California bay and oak trees.

Planning your visit to the Terra Linda Ridge and 680 Trail is straightforward, as the preserve is easily accessible from several neighborhoods. You will find multiple access points, and parking is generally available nearby. This route is a popular choice for various outdoor activities; you can expect to share the paths with other hikers, cyclists, and equestrians. Dogs are also welcome, often enjoying the freedom of being off-leash if they are under voice control. Consider starting your hike in the morning to enjoy cooler temperatures and clearer views.

This trail explores the Terra Linda-Sleepy Hollow Divide Open Space Preserve, an important natural area in Marin County. The diverse terrain and changing landscapes reflect the region's unique ecology, supporting a variety of plant life including California bay and oak trees. The preserve serves as a vital green corridor, offering both recreation and a habitat for local wildlife. Its accessibility and multi-use trails make it a community favorite, providing a natural escape close to urban areas.

Explore the Loma Alta Open Space Preserve on the Loma Alta Peak Trail, a moderate 6.9-mile (11.2 km) hike that delivers stunning 360-degree views from one of Marin County's highest points. You'll traverse diverse terrain, from shaded California bay woods and oak woodlands to wide-open grasslands, culminating in the Loma Alta Summit. Expect a steady climb with 1561 feet (476 metres) of elevation gain, taking around 3 hours and 36 minutes, making it a rewarding challenge for hikers with good fitness.

Planning your visit to the Loma Alta Peak Trail is straightforward, with the White Hill Trailhead serving as a popular access point. Due to extensive sun exposure on the upper sections, an early morning start or a cooler day is recommended. If you hike in winter or early spring, prepare for potentially muddy conditions, but you might also be rewarded with seasonal wildflowers and a delicate waterfall. Always carry ample water, especially during warmer months.

This trail is a highlight for its panoramic vistas, which can include the San Francisco skyline, Mt. Tamalpais, and the Pacific Coast. It's also part of the larger Bay Area Ridge Trail system, connecting you to other open spaces. The preserve's varied ecosystems, from grasslands to woodlands, showcase Marin County's natural beauty, and you might even spot grazing cattle, a practice that dates back over 150 years.

The Oak Manor, Smith Ridge, Sunrise and Old Railroad Grade Loop is a challenging 14.4-mile (23.1 km) hike that winds through a remarkable variety of landscapes in Marin County. Expect to climb 2528 feet (771 metres) over approximately 7 hours and 4 minutes, traversing everything from cool redwood canyons to sun-drenched chaparral and open grasslands. From the top of Smith Ridge, you'll earn breathtaking panoramic views of San Francisco, the Pacific Ocean, and the entire Bay Area, a truly spectacular reward for your effort.

This difficult route requires good fitness and sturdy footwear, especially given the extremely steep sections on Sunrise Fire Road. While much of the trail consists of unpaved fire roads and natural paths, the historic Old Railroad Grade offers a more consistent ascent. Be sure to bring plenty of water and sun protection, as many parts of the trail are exposed. Starting early in the morning or late afternoon can offer the best light for photography and more comfortable temperatures.

A significant portion of the trail follows the Old Railroad Grade, tracing the path of the former Mt. Tamalpais Scenic Railway. Along this historic route, you can spot remnants of the railway's past, including cut-through hills and the famous "Double Bowknot" series of hairpin curves. The trail is a multi-use path, popular with mountain bikers and runners, and is also an important link in the larger Bay Area Ridge Trail system.

The Old Railroad Grade, Glen Fire, Smith Ridge & Sunrise loop offers a dynamic hiking experience, combining historical paths with challenging climbs and panoramic vistas. This moderate 4.9-mile (7.9 km) route, featuring 875 feet (267 metres) of elevation gain, typically takes about 2 hours and 25 minutes to complete. You'll traverse wide fire roads, dirt, and gravel paths, with sections like the Sunrise Fire Road presenting notably steep ascents, while others, like the Old Railroad Grade, offer a more gradual, though sustained, climb. Expect diverse scenery, from redwood canyons and chaparral to open grasslands and sweeping Bay Area views.

Planning your visit to this Marin County gem is straightforward, though awareness is key. Street parking is available, particularly near the Glen Drive starting point for the Glen Fire Road, but it's always wise to arrive early, especially on weekends, to secure a spot. The trails are multi-use, so you'll share the path with mountain bikers and horseback riders; courtesy and awareness of other users are essential. While the loop can be enjoyed year-round, spring brings vibrant wildflowers, and clear days offer the best visibility for the expansive views.

This loop is rich in history and natural beauty, following parts of the