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Hiking trails & Routes
United States
Massachusetts
Berkshire County

Bear Mountain and Mount Race via Undermountain and Appalachian Trail

Routes
Hiking trails & Routes
United States
Massachusetts
Berkshire County

Bear Mountain and Mount Race via Undermountain and Appalachian Trail

Hard

4.9

(9938)

11,431

hikers

Bear Mountain and Mount Race via Undermountain and Appalachian Trail

06:47

21.4km

870m

Hiking

Hike Bear Mountain and Mount Race via the Undermountain and Appalachian Trails, a difficult 13.3-mile route with stunning views.

Last updated: February 26, 2026

Waypoints

A

Start point

Get Directions

2.97 km

Viewpoint

Viewpoint

3.49 km

Viewpoint

Viewpoint

3

3.92 km

Mount Race

Highlight • Summit

6.54 km

Bear Rock Falls

Waterfall

16.1 km

Appalachian Trail Scenic Open Space

Nature Reserve

6

18.7 km

Bear Mountain (2,320 feet)

Highlight • Summit

From an altitude of 2,320 feet, Bear Mountain opens up a magnificent panorama over Mount Washington State Park. The summit is on the Appalachian Trail and is located just before the border between Connecticut and Massachusetts.

Tip by

7

20.4 km

Sage's Ravine

Highlight • Gorge

Sage's Ravine is a popular hiking destination and close to the border between Massachusetts and Connecticut. The long-distance Appalachian Trail runs alongside and there is also a campsite.

Tip by

21.0 km

Sages Ravine Falls

Waterfall

B

21.4 km

End point

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Way Types & Surfaces

Way Types

20.6 km

381 m

300 m

135 m

Surfaces

21.1 km

135 m

111 m

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Elevation

Elevation

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

Highest point (700 m)

Lowest point (230 m)

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Weather

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Today

Saturday 30 May

13°C

6°C

73 %

Additional weather tips

Max wind speed: 23.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

What is the terrain like on the Bear Mountain and Mount Race hike?

The terrain is quite varied and challenging. You'll encounter a consistent, rocky, and rooted climb on the Undermountain Trail. As you merge with the Appalachian Trail, expect steep, rocky inclines, switchbacks, and even some sections with stone steps. Between Bear Mountain and Mount Race, the trail can be steep, with exposed ridgelines and open wooded areas. Be prepared for several stream crossings, especially in Sages Ravine, where you might need to walk directly through water.

Is this trail suitable for beginners?

No, this combined hike is generally considered difficult and requires a vigorous effort. It involves significant elevation gain and steep, rocky sections. Hikers should have prior experience with strenuous trails and be in good physical condition.

What are the main viewpoints and natural features along the route?

This hike offers spectacular scenery. From the summit of Bear Mountain, you'll get expansive views, potentially seeing across four different states and the Berkshires. The summit also features the remnants of an old stone tower. Mount Race provides panoramic easterly views and open ridgelines. A major highlight is Sages Ravine, known for its cheerful brook, rocky formations, and waterfalls. The eastern slopes of Mount Race also feature Race Brook Falls, a series of five cascading waterfalls.

Where is the best place to park for this hike?

The most common starting point is the Undermountain Trailhead. Parking is typically available there, but it can fill up quickly, especially on weekends. Arriving early is recommended to secure a spot.

Does this hike include Connecticut's highest peak?

Yes, this route takes you to the summit of Bear Mountain, which is proudly recognized as Connecticut's highest peak. While the state's absolute highest point is on the side of Mount Frissell, Bear Mountain is the highest summit entirely within Connecticut.

Are there any fees or specific regulations for hiking in Mount Riga State Park?

This trail is located within Mount Riga State Park. Generally, there are no entrance fees for hiking in Connecticut State Parks. However, always check the official Connecticut Department of Energy and Environmental Protection (DEEP) website for the most current regulations, including any specific rules for camping or fires, especially around areas like Sages Ravine.

Is the trail dog-friendly?

Yes, dogs are generally allowed on this trail. However, they must be kept on a leash at all times to protect wildlife and ensure the safety of other hikers. Be prepared for rocky and steep sections that might be challenging for some dogs, and remember to pack out all waste.

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

Late spring through fall is generally the best time. In early spring, sections can have hard-packed snow and ice. Fall offers stunning foliage, but be aware that colder conditions can lead to icy sections, especially on steep descents. Summer is also popular, but be prepared for potential heat and humidity. Always check weather and trail conditions before you go.

Does this route follow the Appalachian Trail?

Yes, a significant portion of this hike follows the iconic Appalachian Trail (AT). This includes a section between Connecticut and Massachusetts that was among the first parts of the AT ever constructed, offering a classic long-distance hiking experience.

Are there any less steep alternatives for reaching Bear Mountain?

While the main ascent to Bear Mountain via the Appalachian Trail can be very steep, an alternative route via Riga Junction offers a less steep approach. This might be a good option if you prefer a more gradual climb, though it may alter the overall length and character of your hike.

What kind of wildlife or plants might I see along the way?

The Undermountain Trail is often lined with Mountain Laurel. Near the summits of both Bear Mountain and Mount Race, you'll find dwarf pitch pines, and scrub oaks are common on the way to Mount Race. During the appropriate season, you might also spot blueberries. As for wildlife, keep an eye out for common forest animals like deer, various bird species, and small mammals.

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