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Routes
Hiking trails & Routes
United States
Vermont
Bennington County

Gilbert's Lookout and Owls Head Trail

Moderate

3.3

(10)

71

hikers

Gilbert's Lookout and Owls Head Trail

02:08

5.72km

410m

Hiking

The Gilbert's Lookout and Owls Head Trail offers a moderate hiking experience through lush forested areas in Vermont. You will cover 3.6 miles (5.7 km) with an elevation gain of 1330 feet (405 metres), typically taking around 2 hours and 8 minutes to complete. The highlight is Gilbert's Lookout, a…

Last updated: April 23, 2026

Waypoints

A

Start point

Get Directions

1

3.22 km

Owls Head

Highlight • Summit

4.46 km

Owls Head Town Forest

Nature Reserve

3

4.95 km

Gettysburg Quarry

Highlight • Structure

Access over Raptor Lane. Nice view over Dorset Valley. Informative plaques along the hike.

Tip by

B

5.72 km

End point

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Way Types & Surfaces

Way Types

5.49 km

224 m

Surfaces

5.55 km

< 100 m

< 100 m

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Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

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Weather

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Today

Saturday 30 May

13°C

3°C

94 %

Additional weather tips

Max wind speed: 18.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

Where is the trailhead for Gilbert's Lookout and Owls Head Trail, and is there parking available?

The trail is located in the Owl's Head Town Forest in Dorset, Vermont. While the exact trailhead location isn't specified in detail, ample parking is typically available at the main access points for town forests. It's always a good idea to check local signage upon arrival.

What is the terrain like on the trail, and how difficult is it?

The trail offers varied terrain, including old roadbeds and steep ascents. While generally considered moderate, sections leading to the quarries and Gilbert's Lookout can be challenging. You'll encounter rocky parts and potentially wet areas with boardwalks. The initial 0.5 miles to Gettysburg Quarry, for instance, climbs steeply. There are different routes, such as the blue trail (steep) and the yellow trail (more gradual).

Is Gilbert's Lookout and Owls Head Trail dog-friendly?

Yes, dogs are permitted on the trail. Please ensure your dog remains on a leash throughout your hike to protect wildlife and ensure a pleasant experience for all trail users.

What is the best time of year to hike this trail?

The best time to hike is typically from April through October, when the weather is most favorable. Autumn offers particularly vibrant fall foliage, making it a popular season. While winter snowshoeing might be possible on some trails in the area, the primary Gilbert's Lookout route is best enjoyed in warmer months.

Are there any permits or entrance fees required for hiking in Owl's Head Town Forest?

No, there are no specific permits or entrance fees required to hike in the Owl's Head Town Forest. It's a public town forest, making it freely accessible for hikers.

What are the main points of interest and viewpoints along the route?

The trail is rich in both natural beauty and history. Key highlights include:

  • Gilbert's Lookout: A rock outcropping with an old marble plaque, offering spectacular panoramic views of the Dorset Valley and the Adirondacks on a clear day.
  • Gettysburg Quarry: A historically significant site where marble was extracted, notably for Civil War headstones. It's a picturesque spot.
  • Art's Bench: A large marble slab near the quarry providing great views across the Route 30 valley.
  • Cellar Holes: Remnants of 19th-century migrant worker houses, adding a historical dimension.

Are there different route options or trails within the Owl's Head Town Forest?

Yes, the trail system offers several options. You'll encounter sections of official trails like the Gilberts Lookout (Blue), Gettysburg Alternative (Yellow), and Gettysburg Quarry (Blue). There's also the Owls Head Loop (Red) and access to other old quarries like Klondike Quarry (Blue). These different blazes allow for varied experiences and difficulty levels.

Is the trail suitable for families with children?

While generally moderate, some sections of the trail, particularly the steep ascents to the quarries and Gilbert's Lookout, might be challenging for very young children or those not accustomed to hiking. The trail description notes that steep sections might not be suitable for young children or individuals with a fear of heights. Consider the yellow trail for a more gradual climb if hiking with kids.

What should I wear or bring for this hike?

Given the varied terrain and potential for steep, rocky, or wet sections, wear sturdy hiking boots with good ankle support. Dress in layers, as conditions can change, and bring plenty of water, snacks, and a map or GPS device. Trekking poles can be helpful for the steeper sections.

Can I hike Gilbert's Lookout and Owls Head Trail in winter?

While the primary hiking season is April through October, some trails in the Owl's Head Town Forest may be suitable for winter snowshoeing. However, conditions can be challenging with snow and ice, and specific winter maintenance or safety information for this particular route isn't detailed. It's best to check local conditions and be prepared for winter hiking if attempting it off-season.

Are there any amenities or places to eat near the trailhead in Dorset, Vermont?

Dorset, Vermont, is a charming town and likely offers local amenities such as cafes, pubs, and accommodation options. While specific establishments aren't listed, you can expect to find places to refuel or stay within a short drive of the trailhead.

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