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Easy and Intermediate Fall Hiking in Southern Vermont

As the weather begins to cool off and the peak of foliage season quickly approaches, it's the perfect time for hitting the trail on a relaxing fall hike. Vermont has an abundance of breathtaking views that gaze into endless mountain ranges and look down over the peaceful towns that make up the unique countryside.

Hiking in Vermont offers many thrills to outdoor enthusiasts. Photo opportunities, animal sightings and friendly encounters with other hikers are a part of every outing.  In addition, the difficulty of the terrain varies greatly and accommodates all ranges of interest and skill. For trips out with the whole family, try these easy to intermediate hikes just a short drive from Wilmington.

Hogback Mountain Conservation Area

View from the fire tower at Mt. Olga. Marlboro, VT

One of Vermont's forgotten ski areas, Hogback Mountain continues to be a frequented hike for visitors traveling along Route 9 between Marlboro and Wilmington. There are several trails accessible inside the boundaries of the conservation area. The Tower Trail is a popular route and starts next to the Hogback Mountain Gift Shop. Follow the old ski trail just over 0.5 miles west to the fire tower at the peak of Mt. Olga (elevation 2,418'). Climb the spiraling staircase and you'll be rewarded with a stunning 360 degree view spanning from the Green Mountains (north) to the Berkshires (south).

Mount Wantastiquet

View of Brattleboro from the summit of Mt. Wantastiquet.

For a unique view of downtown Brattleboro and the Connecticut River there is no better choice than Mt. Wantastiquet. Take Rte. 9 into downtown Brattleboro, head down Main Street and cross the iron bridges into Hinsdale, New Hampshire on Rte 119. Take the first left and follow the dirt road to the end. From there two trails begin to the north. One follows the banks of the Connecticut River with easy climbs for two miles. The other switchbacks up a rocky old road bed for just over two miles to a rock outcropping at the summit. Shortcuts along the way can cut down on time, but they are steep, narrow and cover more rugged and uneven terrain. Make sure to wear shoes with good traction if you venture on these routes.

Putney Mountain Summit

Panoramic view from Putney Hawk Watch.

Also known as the Putney Mountain Hawk Watch, this a favorite spot for bird lovers. Located on the Brookline/Putney town line, the Hawk Watch is an easy hike to gorgeous views of the surrounding valley and distant mountain peaks including Stratton, Mount Snow, Bromley, Haystack and Mt. Manadnock in New Hampshire. For year round access, head north from the center of Putney on Westminster Road, turn left onto West Hill Road and continue past the apple orchard. Turn right on Putney Mountain Road and follow it to the peak (roughly 2.2 miles) where there is a parking area on the right and a kiosk. Hiking to the summit takes less than 30 minutes, where a message board lists the bird sightings for the season along with bird identification tips and images.

When you're ready to kick off your hiking boot, consider putting your feet up in one of our short term rentals just a short commute from the trail head.

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  1. Patty Killion on

    […] views. Between the mountains and the huge expanses of forest, Vermont is a great place to take a hike, and these three Vermont hiking trails offer some of the best views you’ll find anywhere in […]
    • Ann on

      Sydney LongfellowI used to work at the Brattleboro Food Coop until I moved to Northern California. Now I work at a locally owned naatrul foods market called The Good Earth. On February 15th we moved into our brand new expanded location down the street from the older store. We renovated an old eyesore in town to create our new store: we expanded all the departments, added parking, landscaped, renovated the building with green technology and used local artists to beautify, and even added new departments plus tons more selection in our deli and hot food. Many people loved it immediately, but lots of the regulars were aghast: it's just like Whole Foods , it's too big , it's impersonal , you ruined my local grocery store, etc. Nearly five months later the furor has quieted down and I think I can safely say, now that everyone has gotten over the shock, that most people enjoy the new store. Sales are up and everyone is happy and friendly again. I'm sure it will be the same for the Coop in Brattleboro. I can't wait to see it when I visit town in August!
      • P.O. BOX 415, 9 Haystack Road, Wilmington VT 05363