to preserve and promote the natural beauty of the Hilltowns of Western Massachusetts

…we recognize and preserve Hilltown history for all…

Mission Statement: Western Mass Hilltown Hikers, Inc. is organized exclusively for charitable and educational purposes to engage in all legal activities relating to the development, maintenance and operation of recreational hiking and outdoor adventure in Western Massachusetts.

Western Mass Hilltown Hikers, Inc. provides monthly, free group guided tours of hiking locations in various locations of Western Massachusetts. We also provide free volunteer trail maintenance for trails including brush clean up, trash collection and storm cleanup for all outdoor passive recreations in Western Massachusetts. We also provide free presentations to other civic groups, non-profit organizations, libraries and schools.

We are a non-profit 501C(3) organization incorporated in the State of Massachusetts. Tax ID #86-2532249

The Hilltown Hikers will be at Chester on Track all day in historic downtown Chester with a booth on Main Street and Riverfront next to the Riverside Inn aka Chester Hotel. we will have our entire catalog of hiking maps, shirts, hats. hoodies, photo prints, puzzles, animal track guides, Hilltown history, photos, and ALOT of hilltown hiking information! come see us, ask us questions, get trail info!

and there’s more!

CHESTER ON TRACK RETURNS FOR A 31st SEASON May 21, 2022, CHESTER, MASSACHUSETTS. The 31st anniversary Chester on Track marks the 181st year since the rail road was opened. The Station was granted National Historic landmark status in January of 2021. MA Dept. of Conservation and Recreation will serve as guides to assist visitors get maxi mum exposure to the Keystone Arches, the first cluster of stone arch railroad bridges built in America. Also National Historic Landmarks. There will be a massive parade, Civil War, Revolutionary War and early Irish railroad re-enactors, will be on the north lawn of the station. A train show will be in the station, and The Chester Postmaster will be on hand to personally cancel the commemorative envelopes with a special postal cancellation. A ham radio base camp will be on hand to contact enthusiasts around the globe and doing Morse code demos. A craft fair, face painting and ‘one-lung’ steam & gas engine demos will be along Main St and on the lawn of the Chester Inn with live music throughout the day by the group, Just Us’. A ham radio base camp will be on the Station platform, contacting bases around the globe and demonstrating Morse code. Classic cars from Model ‘T’s to the newest Corvettes will line up on Maple St., where kids can visit the bounce house, and be entertained by Nicole the Rail road Clown, formerly of Ringling Bros. Circus. Chester/ Blandford Police Dept. and Sherriff’s Department will be on hand to introduce and explain new community programs. The railroad station outdoor stage will host live music beginning at 11 AM with the 413’s, Pug Demary, Pitoniak Brothers, Mark Franklin and the Fortified Blues Band. The Pioneer Valley Live Steamers will display their large-scale operating steam and diesel locomotives and a selection of rolling stock on the station’s south lawn. The Hamilton Library will hold a Book and Bake Sale on the lawn, and the Library’s ??Chester Mineral Collection will be open for tours with John Marge from 10 AM to 1 PM. ??The Chester Historical Commission will be on hand at the Old Jail and Chester History Museum for tours from 9:30 AM to 3:30 PM?? The Foundation’s own Blue Caboose will open at 8 AM for breakfast and have a hearty railroad man’s menu. throughout the day, where you can cat ‘hobo style’ in an antique wooden box car. Carm’s and Classic Pizza will be open all day as well as The Village Market for take-out. A number of 1920’s-era freight cars, including a 100 year-old wooden caboose and ‘Children’s Boxcar’ will be open to the public. The Fire Dept. will hold their annual Duck Race on the Westfield River at 2:00 PM. 
We updated this website platform in Fall 2020 after completely outgrowing our old one! That being said,  we will be uploading ALL our info here…yes..everything, including dedicated pages to Hilltown History and a more user friendly map database.  Don’t forget our BLOG has everything we do including new map uploads.  Thank you, we love you guys!

Watch Karen and Liz on the Live Broadcast of Ken’s Den on WCPC15 TV (Westfield Public TV) and WSKB 89.5 FM (Westfield State Radio).  Thank you to Harry Rock and Kathleen Palmer for an enjoyable morning on LIVE TV! 

Special Thank you to Patrick Berry and Mass Appeal for coming out to Chester! 
(Mass Appeal) – There are many miles of hiking trails in Western Massachusetts and one group has been regularly organizing hikes and volunteer efforts to maintain some of these trails.
Liz Massa, Lead Hiker and volunteer with the Western Mass Hilltown Hikers, gives us an inside look at some of the hikes and history they’ve been enjoying.
The 2022 20th Annual Housatonic Heritage Walks are out! We are pleased to be hosting and co-hosting TWO hikes this year!!

Western Mass Hilltown Hikers was created for people who love the outdoors to get out and discover new destinations for outdoor recreation.  Our goal is to bring awareness of the landscape, history and wildlife the Hilltowns of Western Massachusetts have to offer and promote those natural assets to boost tourism and economic development to the area while still keeping our open spaces natural.

In 2016, we decided to take YOU along……

We were once three friends who hiked every weekend to a different destination, each week more friends joined us, then friends of friends and so here we are today, a group of over 10,000 members, over 3,500 in the Facebook Group and 7,000 followers on our Social Media platforms.  Each month we lead a publicly advertised group hike, always free and no registration required (except during COVID), open to everyone including well behaved dogs.
We want to hear from you!  Do you have a great hiking destination?  Historical location?  Are you a landowner with awesome trails and want to do a group hike? Email us at westernmasshilltownhikers@aol.com 



Special Thanks to Andrea at the Greenfield Recorder for an awesome story on getting out there and staying healthy with the Western Mass Hilltown Hikers!

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This is where you will find our latest stuff, it’s good…



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Upcoming Events

Shatterrack Mountain in Russell

Keystone Arch Bridges Trail in Chester

Tekoa Mountain in Montgomery

I invite you all to post on all our social media your adventures whether it be hiking, cross-country skiing, snowshoeing. kayaking or mountain biking.  Let others know your idea for a hike or share your favorite trail. Post your beautiful pictures and videos! If you are looking to get out there and you need someone to come along…. you can network on our social media. We use hashtags to find our adventures all over the internet, #westernmasshilltownhikers and #hikethehilltowns
I have discovered that there are many of you out there that want to get outdoors to a waterfall or climb a mountain and need a partner to do it with or simply want to enjoy our pictures and videos. I invite you to all come out to the Hilltowns of Western Mass to see and enjoy our natural beauty! 

Hike Leader Liz

I have been told that I am a “hike-a-holic”.  Fact, I am!  I rented a house in Richmond years ago, hiked/biked the area trails and remembered how much I enjoyed growing up in the woods of Hampden.  After working and living in the Springfield area for 20 years….it was time for me to get back in touch with the outdoors.  I immediately made the move to Russell after completely falling in love with the Hilltowns and finding myself again.  There is nothing I love more than our beautiful Hilltowns and my dogs of course!



Ronnie is a 14 year old Lhasa Apso who has hiked the Appalachian Trail in Massachusetts.  She loves mountains and rock climbing.  Find her on the trail at Liz’s feet. Ronnie has recently gone blind, she continues to be a happy dog but unfortunately she cannot hike with us any more as she has gone into retirement.


Angie loves to hike but preferably in warm weather! Angie loves other dogs and people. Hide your trail snacks, she loves food too.

Hike Leader Karen

Karen McTaggart grew up in Russell.  After being away for 30 years in Southwick and Agawam, she moved back to town to help her Dad, Gerry Sikes.  She is a postal carrier in Suffield, Ct and has a son and granddaughter in LA, whom she loves to visit.  Karen is an original Western Mass Hilltown Hiker and Hike Leader.  She was an avid softball player and played for the Russell Inn Woman’s Softball Team in the Hilltown Women’s League.  Karen loves to travel, having family all over the country.  But, returning to the beautiful hills of home is her favorite thing.  Local history and family genealogy is her passion.  This makes for a great enjoyment for hiking the local roads, trails, and woods, as well as the beautiful views.  Bowling, hiking, photography are her activities of choice.   Karen is an original founder along with Liz of the Western Mass Hilltown Hikers.


Hike Leader Michele

Hike Leader Michele Kenney has lived in Western Mass for over 30 years, with 20 of those years in Chester. Michele hikes with her two dogs: Kiki, a flat coated retriever mixed with chow, and (Taco) Bella, the famous WMHH Chihuahua.

When not hiking, Michele could be found kayaking, or making thermal shades for her business CustomThermalshades.com

Michele also is the program director of the Southern Hilltowns Adult Education Center, does Business Assistance for the Hilltown CDC, and is an active member of the Jacobs Ladder business Association.



Hike Leader Lyle

Lyle grew up in Connecticut and got her first real taste of hiking when she walked across Europe in college. Later she moved to Colorado where she spent time exploring the San Juan Mountains. A couple years ago she finally settled down in western MA and has been hiking and exploring the area since. She also has her best furry friend, Finley, with her on hikes. If you’ve been on a hike with WMHTH you’ve probably seen him and his sheer excitement to hit the trails!


Hike Leader Kim

I am originally from South Hadley, Ma. and currently living in Huntington for the past 10 years.
I work as an HVAC Coordinator for small family owned company.  My favorite hobbies are hiking, gardening, cooking, fishing and painting oils and acrylics on canvas.  I also enjoy music, motorcycle rides, antiques, cape cod and my family and my two kitty cats.    




Hike Leader Russ

Grew up in South Jersey when it was still rural.  Worked on a Thoroughbred training farm and spent a lot of time walking in the woods.  Hiked and backpacked many of the national parks in the west and upper midwest including off trail route finding in few national parks.  Also backpacked in Puerto Rico.  Flown in by bush plane close to Chitna glacier (Alaska) and paddled back.  Have hiked four 14ner summits including Mt Whitney (on the first attempt).   Thoroughly spoiled by the Rockies.  Moved to hill towns just before Covid lock down.  Spent initial few months beginning to learn the area alone due to Covid.  To do list includes PCT and CDT.  Retirement plans include much time in Alaska, interpretive rangering in National Parks system and international volunteer large animal vet medicine. 



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