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Blog :: 09-2011

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.


  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!

      Mount Snow OktoBrewFest and Golden Chair Raffle

      Never fear brew fans, the time for beer is near. If Hurricane Irene thought the flooding and destruction was going to stop a great beer drinking tradition in Vermont, she was sorely mistaken. In fact, it has made the community stronger and the festivities bigger. Get ready for OktoBrewFest coming October 8 & 9, 2011.

      Forging two great Mount Snow annual events -- Oktoberfest and the Brewer's Festival -- OktoBrewFest is sure to be a schnitzel and beer extravaganza the like's of which have never been seen, not even in Germany. So grab your drinking buddies, strap on your lederhosen and get ready to polka.

      Shop around for great Vermont products at the Harvest Arts and Craft Show. Browse the extensive tap list from local and national breweries and sample delicious fall offerings from Beck's, Sam Adams, Harpoon, Wolaver's, Long Trail, Dogfish Head, Ayinger, Trapp, Victory, Rock Art, Rouge and many more.

      Games and activities for kids including face painting, pumpkin painting, arts & crafts, a hay pile and the famous "schnitzel toss". Adults can compete in a keg toss, Horseshoe Tournament, and Stein Holding contest.

      Plus, don't forget to grab a ticket for the Golden Chair Raffle, and earn a chance to take home a piece of the mountain's history. All proceeds from the raffle benefit Vermont flood recovery efforts in the area. The chair has been freshly painted and hung on a custom-built timber frame. The lucky winner will be drawn at the start of the ski season.

      Admission: One Day: $25 - 21+ Adults /$12 - Under 21 / Kids 5 & Under Free Two Day: $35 - 21+ Adults / $20 - Under 21 / Kids 5 & Under Free

      All 21+ adult admission receive a special commemorative pint glass.

      If you overfill on sauerkraut and lager we've got plenty of rental homes near Mount Snow for you to hang up your laderhosen.

      WHAT: OktoBrewFest and 38th Harvest Arts and Craft Show WHEN: October 8 & 9, 2011. 11:00 AM to 5:00 PM WHERE: Mount Snow base area, West Dover, VT

      Wilmington, VT/Chimney Hill update, donation information. Irene flood.

      Here is an update of road conditions and relief efforts in the Chimney Hill and Wilmington, Vermont area as of Monday, September 5, 2011. Tropical Storm Irene hit Vermont on Sunday, August 28, causing widespread flooding. Wilmington was one of the hardest hit areas in the state.

      2011 and 1938 flood level, wilmington, vermont

      Access in and out of the area is still limited. It is hoped that at least one lane on Route 9 from Bennington will be open by the end of the week (bridge above the Woodford School) and Route 9 from Brattleboro is still being worked on below Marlboro and only open to emergency and relief vehicles at this time. As of this writing the Route 9 Bridge in Wilmington has limited vehicle access and foot traffic is prohibited.

      You can get to Chimney Hill via Route 2 in Greenfield to Route 112 and then route 100. You will need to take Route 100 north in Wilmington to Cold Brook Road and then gain access to Chimney Hill via Mann Road (past the Haystack golf course) to upper Ray Hill Road which will bring you to the upper end of Haystack Road. Because the Town has been busy putting the infrastructure back in order in the downtown area many roads in Chimney Hill still are one lane with steep drop offs on the sides, please use caution when getting around the Hill and local areas. We have been told that the Town will begin road work in Chimney Hill this week. Chimney Hill will begin contacting those owners who have experienced driveway washouts this week with estimates on repairs. Driveways repairs may take some time as materials for repairs are limited.

      It is amazing how much has been done in a week. Hundreds of volunteers worked around the clock to clean out the downtown area. Our maintenance department assisted in these efforts helping the Wilmington Water Department in getting their system back in order and removing piles of debris from the downtown area. We also assisted the Chamber in relocating their offices to the Split Ends building (up the street from the Town offices).

      There is much that still needs to be done and we all want our town to recover from this devastating flood and return our area to the great place we have all come to enjoy, and it will.

      As many of you have offered your assistance of help the following relief sites have been established and are accepting donations. We have been assured that all of the sites listed will use all of the monies donated for the local community. When and if you make a donation please let them know that you are a Chimney Hill owner.

      Specific Local Funds:

      FOR TOWN INFRASTRUCTURE: The Town of Wilmington has set up a Flood Relief Fund.  To make donations please make out checks to "Town of Wilmington Flood Relief Fund" and mail to Town of Wilmington, PO Box 217, Wilmington, VT 05363. This fund is to be used to help the Town defer our costs to rebuild infrastructure.  Donations are tax deductible and you will receive an acknowledgement by mail.

      FOR WILMINGTON SMALL BUSINESSES:  Wilmington VT Flood Relief. Unfortunately, flood insurance and FEMA rarely give support to businesses that lose inventory or equipment. This relief fund, with coordination through the Deerfield Valley Rotary Club and Mount Snow Chamber of Commerce, has been set up to help offset any replacement costs or repair expenses. PayPal donations link at the website. They are working on getting 501c3 status and will update accordingly. All donations will be dispersed to local Wilmington businesses exclusively.

      FOR FAMILIES: Deerfield River Valley Human Webwww.drvhumanweb.com

      These funds will be used to help affected families anywhere along the Deerfield River path.  People will be able to apply for grants from this fund to help displaced renters, people who have lost work and jobs because of the flooding, lost furniture, etc.  A website with more information will be set up soon.  For now, checks made out to "Deerfield River Valley Human Web" can be sent to the fund at 14 Castle Hill Road, Wilmington, VT 05363.

      One of our own, a Chimney Hill staff member, also had flood damage to their home in Wilmington center. Although somewhat covered by insurance they lost many of their personal items and have expenses not covered by insurance. If you wish to make a donation please send your check to: Chimney Hill Owners Association, P.O. Box 415, Wilmington, Vermont 05363. Checks should be made out to Chimney Hill and include in the memo section "Staff Relief".

      In lieu of monetary donations:

      Furniture, small appliances, etc. - Wahoo Eatery Flood Relief - contact Adam Grinold (802) 780-7828.

      Clothing and "Stuff" - Twice Blessed, (802) 464-7500. Clean and in good shape clothing and household items can be dropped off at 716 Route 100 North, Wilmington.

      Food Donations - Deerfield Valley Food Pantry - non-perishable food donations accepted. Open from 9 AM to 5 PM daily at 7 Church Street, Wilmington (802) 464-0148.

      Time heals all and this will hold true for our area. With your help homes, roads, infrastructure and businesses will be reconstructed and our great corner of Vermont will be open for business as usual.

      The concerns and generosity of our membership is overwhelming and all of us in the local community thank you for your past and future support.

      I will keep updating the membership as developments warrant.

      Very Sincerely,

      Ken Spicer Executive Director Chimney Hill Owners Association, Inc.


      1. edythe darnell on

        My family in NYC is naturally concerned about me being up here alone. I.m ok, but if they decide to come up here to "rescue" me next week, what would be the best route-from NYC perhaps using Rte 91 or an alternative? Thankyou, Edythe 15 Corner Lane
        • edythe darnell on

          In case my family from NYC want to "rescue" me what is the best route? 15 Corner Lane B53
          • admin on

            Edythe, there is detailed information on the condition of roads and the routes in and out of Chimney Hill in the post above. Once your family has reached Greenfield, MA they can follow the directions below. You can get to Chimney Hill via Route 2 in Greenfield to Route 112 and then route 100. You will need to take Route 100 north in Wilmington to Cold Brook Road and then gain access to Chimney Hill via Mann Road (past the Haystack golf course) to upper Ray Hill Road which will bring you to the upper end of Haystack Road.
            • P.O. BOX 415, 9 Haystack Road, Wilmington VT 05363