25 Self-Guided Hikes in Western MA to Support Place-Based Learning

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Here is a list of self-guided hikes to do with your family or on your own. To support place-based learning, before you head out, conduct an online search about the natural and human history of some of these community-based educational resources. Bring with you field guides, sketchbooks, cameras, and magnifying glasses and spend the afternoon engaged in self-directed, nature-based learning!

Easy Hikes in Western MA:

  • Chesterfield Gorge, West Chesterfield
  • Dinosaur Footprints, Holyoke
  • Field Farm, Williamstown
  • Mass Audubon Pleasant Valley, Lenox
  • Mass Audubon Arcadia, Easthampton

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Land Trusts & Native Species: Community-Based Educational Resources to Support Self-Directed Learning

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Self-guided hikes are a great way to keep your family active outdoors and engaged in nature! They’re also excellent ways to support learning via community-based educational resources, including land trusts & native species!

Download this free interpretive trail guide Hilltown Families created with the Hilltown Land Trust for the Bradley Sanctuary trail in Williamsburg, MA. This guide goes beyond the typical map and route. It highlights interesting features and information from cultural, scientific, artistic, and historical perspectives. It encourages users to think about how their experience outdoors relates to other interests such as citizen science, history, literature, and social activism. Additionally, it complements the trail guides by providing additional resources and activities that extend your learning off the trail.

This guide takes hikers along the Red Oak Trail, a great walk to do with kids or on your own. On this trail, hikers will see the historical and environmental features of Bradley’s landscape and enjoy a lovely walk along Nichols Brook. One of the most interesting features of the Bradley Sanctuary is an old-growth Red Oak tree that is approximately 5 feet in diameter. Included in the guide is a formula for helping Bradley hikers hypothesize the tree’s age.

This property is available to the public year-round, thanks to Hilltown Land Trust’s land conservation efforts and the foresight of Hilltown residents who value the protection of our natural resources in perpetuity for future generations to visit and love. Each Hilltown Land Trust property has a story to tell. This partnership with Hilltown Families narrates this story for Bradley Sanctuary in Williamsburg, MA, and shows how our community places are connected to our personal stories and interests.

Use this guide to strengthen your relationship to the local land and experience these Hilltown forests and woods in new and inspiring ways.

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4 Guided Hike Resources in Western MA

Guide Hikes Connect to Nature

In The Maine Woods (1864), Henry David Thoreau writes:

Talk of mysteries! — Think of our life in nature, — daily to be shown matter, to come in contact with it, — rocks, trees, wind on our cheeks! The solid earth! the actual world! the common sense! Contact! Contact! Who are we? where are we?

Franklin Land Trust. Guyette Farm in Plainfield, MA (c) Sienna WildfieldBefore asking the questions “Who are we? Where are we?” Thoreau already provides his readers with the solution to discovering the answers: “think of our life in nature,” He urges the reader to come into contact with nature – to experience the natural world. This interaction with the outdoors can help us build a deeper sense of self and place – hence Thoreau’s final questions are left unanswered to provoke the reader, as if the author is directly telling you “go outside and discover! See yourself in nature, as a part of it!”  Read the rest of this entry »

25 Self-Guided Hikes in Western MA

Self-Guided Hikes in Western Massachusetts

Bullitt Reservation in Ashfield, MA (c) Sienna Wildfield

Bullitt Reservation in Ashfield, MA. (c) Sienna Wildfield

The following is a list of places to discover in your community with friends, family, or on your own. Before exploring, become aware of the literary, artistic, and historic connections that some of these places offer.

Easy Hikes in Western MA:

  • Chesterfield Gorge, West Chesterfield
  • Dinosaur Footprints, Holyoke
  • Field Farm, Williamstown
    Field Farm features a garden with 13 modern sculptures, including works by artists Henry Ferber and Richard M. Miller. For architecture enthusiasts, the artistic play between Field Farm and The Folly’s mid-century design elements and the natural landscape surrounding them is compelling.

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Explore the Local Landscape and Local History with Hike 125

Explore the Local Landscape and Local History with Hike 125

Alongside camping, hiking stands as one of summer’s most classic family activities. The leafy canopy afforded to hikers on forest trails makes the woods a cool and inviting space to explore, and the potential for exploring nature at its greenest and liveliest is enticing for adventurers of any age. From short afternoon hikes to serious treks, the trails of western Massachusetts have much to offer adventurous families.

On top of the many benefits of hiking is an added bonus this summer, related specifically to local trails that are part of properties maintained by the Trustees of Reservations. To celebrate the organization’s 125th anniversary, the Trustees are holding the Hike 125 challenge, a celebratory event that challenges locals to hike 125 (or more) miles of the Trustees’ trails before December 31, 2016. In addition to a strong sense of accomplishment, heightened awareness of natural phenomena, stronger muscles, and a deepened sense of place, all participants attempting to rise to the challenge will be entered to win special prizes – with those who manage to hike at least 125 miles entered to win the best prizes of all.  Read the rest of this entry »

Poetry & Place in the Hilltowns

Poetry & Place: Exploring the Hilltown Home of 19th Century Poet William Cullen Bryant

By Andrea Caluori-Rivera
MassLIFT AmeriCorps Member at Hilltown Land Trust & Kestrel Land Trust

Kindred Spirits was commissioned by the merchant-collector Jonathan Sturges as a gift for William Cullen Bryant in gratitude for the nature poet’s moving eulogy to Thomas Cole, who had died suddenly in early 1848. It shows Cole, who had been Jonathan Sturges mentor, standing in a gorge in Catskills in company of a mutual friend William Cullen Bryant. Painting is by artist Asher Brown Durand (1796–1886).

Western Massachusetts has been home to many poets and writers who were inspired by this region’s remarkable landscapes and natural settings. Since April is National Poetry Month, the spring season is a great time to explore some of the homes and writing places of local poets from the past, such as the William Cullen Bryant Homestead in Cummington, MA.

William Cullen Bryant (1794-1878) was an editor, abolitionist, conservationist and poet. He grew up in Cummington, MA and later purchased his childhood home and converted it to a country house. Known for his poems inspired by nature, Bryant was also well acquainted with prominent Hudson River School painters Thomas Cole and Asher B. Durand. The three of them used their artistic talents in painting and writing to champion the American landscape and helped to inspire the American conservation movement. You can read more about Bryant and his life here: www.poetryfoundation.org.

The William Cullen Bryant Homestead, now a property of The Trustees of Reservations, houses a wonderful collection of items from Bryant’s lifetime as well as interesting objects from later decades left by Bryant’s descendants and those that lived there. The property also boasts an old growth forest and a trail system that follows a rivulet – a water feature Bryant wrote about in 1823 in his poem The Rivulet. Read this poem and his most famous, Thanatopsis.

This spring and summer, The Trustees of Reservations have a variety of activities planned for folks at the homestead where visitors can volunteer, experience history and learn more about this interesting place and its antique objects. These events offer a variety of opportunities to engage your local community through different interests such as community service, local history, poetry, food traditions, and ecology, and hiking.  Read the rest of this entry »

Discovering Place with Hilltown Land Trust & Hilltown Families’ Trail Guides!

Explore Someplace New with Hilltown Land Trust & Hilltown Families’ Trail Guides!
By Andrea Caluori-Rivera

Hilltown Land Trust and Hilltown Families have joined together through a shared love of the land to offer free interpretive trail guides that connect families to local Hilltown hiking spots. The properties are all owned by Hilltown Land Trust and are available year round for public use. Each property offers a variety of paths to walk and explore forests, waterways, and wildlife habitat. The guides are accessible online and can be downloaded from the Hilltown Families’ website.

Exploring the natural world in our communities helps us construct a sense of place. By interacting with the land, we learn more about local history, land use practices and the importance of cultivating a meaningful relationship with nature.  Spending time outside offers space for activity and thoughtfulness; it’s an opportunity to recharge and feel more connected to your community.  These trail guides go beyond the typical map and route. They highlight interesting features and information from cultural, scientific, artistic and historical perspectives. They encourage users to think about how their experience outdoors relates to other interests such as citizen science, history, literature and social activism.  Additionally, the A Sense of Place guide complements the trail guides by providing additional resources and activities that extend your learning off the trail.  Read the rest of this entry »

State Forests & Parks: Treasure for all to Enjoy

Massachusetts State Forests & Parks Connect Community to Local Habitat and Natural Resources

In the extreme southwest corner of Massachusetts is a cluster of state parks noted for their spectacular scenery and breathtaking views, including Mount Washington State Forest. Adjacent to the state forest is Bash Bish Falls, one of the state’s most dramatic waterfalls. Cascading water tumbles through a series of gorges, and then plummets some 60 feet into a sparkling pool below. One of the many “so much fun for so little money” locations the DCR manages.

  • “Come out and play!”
  • “Find yourself in a state park.”
  • “It’s your nature.”

These are some of the phrases Massachusetts Department of Conservation and Recreation (DCR) has used over the years to invite visitors to Massachusetts state Forests and Parks.  They are all true. Here’s another one:  “So much fun for so little money!” It’s unofficial, of my own invention, and so true, too.

The Massachusetts Department of Conservation and Recreation – the state forests and parks – kicks its recreation season into high gear in June.  Plan a visit.  Plan lots of visits.  Let’s talk about the “so much fun” part first.  “For so little money” is covered later in this article.


The first thing to know about your state Forests and Parks is that there are lots of them – approximately 150 sites throughout Massachusetts. They range from small “pocket parks,” such as playgrounds, in eastern Massachusetts, to several thousand acre forests in western Massachusetts. October Mountain in Berkshire County, at over 16,000 acres, is one of the largest.

The point is this:  Each park is special in its own unique way, whether it is a geologic wonder, like Natural Bridge‘s marble formations in North Adams; or the state’s highest peak, Mt. Greylock State Reservation, in Lanesboro; or waterfalls like the 80-foot Bash Bish Falls in Mt. Washington; or even re-claimed forest land, such as Erving State Forest and many of our other state forests. Read the rest of this entry »

Hiking at Night at Bear Hole

Family Night Hike at Bear Hole
Saturday, November 2nd in West Springfield

Invite yourself to the opportunity of experiencing a side of the Bear Hole watershed that many do not experience… at night! Bear Hole is much different at night. Many creatures come to life at night and with winter around the corner and mating season for some animals in motion. Hear sounds that you’ll never hear during the day.

Many animals are well-equipped for night hunting and travel; some even prefer it to daytime prowling. Animals of different species have a variety of adaptations that make navigating field and forest simple in the dark – things like echolocation and slit-shaped pupils mean that the setting sun doesn’t dictate the end of an adventure. Humans, on the other hand, have an entirely different experience with darkness. Our eyes, with our rounded pupils, are not designed for excellent night vision, and our other senses are not as sharp as those of other creatures – facts that make explorations in the dark challenging, spooky, and quite different from the sensory experiences that we’re used to.

The West Springfield Environmental Committee is offering families a chance to explore the dark nighttime woods for themselves on a guided hike at Bear Hole! Taking place at 6:45pm on Saturday, November 2nd, the hike will take participants on a shadowy three mile trek through the trails of the city of West Springfield’s heavily wooded municipal watershed on 1700 acres with 20 miles of trails and footpaths. Guided by flashlights and headlamps, families will listen to the noises of night creatures, smell the scents of a sleepy wood, and see a familiar type of landscape in a new light (er, lack of light)…

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Summer Hiking Adventures at Mount Greylock State Reservation

9 Hiking Adventures For All Ages in the Berkshires

Join state park interpreters this summer for fun, family-friendly explorations on Mount Greylock State Reservation. For all programs, be prepared for weather, bring a snack and water. Sponsored by the Department of Conservation and Recreation. For more information contact 413-499-4262.

Get outside and explore a local mountain (and landmark!) with the family this summer!  The Massachusetts Department of Conservation and Recreation is offering nearly ten different weekly hikes throughout the summer at Mount Greylock State Reservation, the highest point in the state of Massachusetts.  Families of all ages and hiking abilities will find multiple opportunities each week to venture to various parts of the reservation – hikes highlight everything from waterfalls to local flora and fauna, hiking and woods skills to summit habitats.

Families with young children can introduce small kiddos to the wonder of the natural world and the fun of hiking at the weekly Tyke Hike, an easy and slow woods adventure that ends with a nature-themed storytime.  Older kids can enjoy more strenuous hikes or take part in Hiking 101, designed to teach confidence on the trails and equip participants with the skills necessary to become seasoned hikers.

Along with introducing kids to the love hiking, the weekly adventures provide families with regular opportunities to engage with and learn about their local surroundings…

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5 Hikes for Families in Western MA State Forests and Parks

Take a Hike!
Explore the State Forests and Parks of Western MA

Outdoor explorations can also supplement students’ studies of local ecology – bring a field guide and learn to identify the many different trees, flowers, etc. that you discover.  (Photo credit: Sienna Wildfield)

Explore the hills of Western Massachusetts – spend an afternoon hiking at one of the many local state forests and parks!  The Massachusetts Department of Conservation and Recreation (DCR) offers families an outline of hikes at numerous locations all over the Hilltowns and Berkshires, including the DAR State Forest (Goshen, MA), Western Gateway Heritage State Park (North Adams, MA), Pittsfield State Forest (Pittsfield, MA), Mohawk Trail State Forest (Charlemont, MA), and the Tolland State Forest (Otis, MA).

Their guide, Take a Hike! Explore the State Forests and Parks of Western MA,  shares information on finding and following trails, as well as length of hike, difficulty, and interesting highlights that families can see, explore, and learn about on each trail.  Hikes make a great summer adventure for families, but are also great through the fall (until it snows, then break out the snowshoes!) and in spring, as leaves begin to appear.  Explore the many different hikes suggested, and find a family favorite!

Outdoor explorations can also supplement students’ studies of local ecology – bring a field guide and learn to identify the many different trees, flowers, etc. that you discover.  To check out the hikes, download their guide,  Take a Hike! Explore the State Forests and Parks of Western MA.


Golden Guides from St. Martin’s Press are beginner field guides that offer an introduction to different outdoor classifications that are easy to used for any family just starting their outdoor explorations together. Pick up a guide on a particular topic your kids are interested in exploring while hiking our local state forests and parks, and go on a quest together to find and identify parts of our natural habitats:

First Day Hikes in Western MA

DCR Sponsors First Day Hikes

“What better way to kick off the new year than with a hike at a state park?” said DCR Commissioner Richard K. Sullivan Jr. “Think of it as the start of a new and healthy lifestyle, for the whole family. Please join us outdoors on New Year’s Day.” (Photo credit: Sienna Wildfield)

The Department of Conservation and Recreation (DCR) will sponsor free “First Day” family hikes in 14 state parks across the Commonwealth on New Year’s Day, as a way to connect children and parents with the great outdoors even – or maybe especially – in winter. Several will be here in Western MA.

First Day hikers can expect to be surrounded by the quiet beauty of nature in winter, with views and vistas unimpeded by foliage. Wildlife that might be spied along these walks will almost certainly include song birds, turkeys and bald eagles. If you do see a Bald Eagle, remember that MassWildlife is holding their Midwinter Bald Eagle survey period right now through January 12, 2011. Everyone who is outdoors and sees an eagle during this time period is encouraged to report his or her sighting! You can send your report to mass.wildlife@state.ma.us. Please provide the date, time, location, and town of eagle sightings, plus the number of birds, whether juvenile or adult, and your contact information.

If you’re lucky (and quiet), you might also catch sight of a red fox, moose, porcupine or fisher.  The Massachusetts Division of Fisheries and Wildlife Pocket Guide to Animal Tracks can help identify which animals may have passed by.

DCR’s First Day Hikes in Western MA include:

The DCR advises that in preparation for each hike, pay close attention to the details of starting time and location. Dress warmly. Wear layers of clothing and sturdy, warm hiking boots or shoes, as well as hats and gloves. Binoculars always come in handy, and do bring water.

In the event of inclement weather, please call 617-626-1450 after 3 p.m. on December 31 for any possible cancellations.  All hikes will be led by park staff members and will last about two hours. Participants are urged to arrive half an hour early to register. For details, visit www.mass.gov

Other (non-DCR) first day hikes:

  • 10am: First Day 2011 Hike with Williamsburg Woodland Trails at Bradley Sanctuary.  Directions here. 268-7523 Williamsburg, MA (FREE)

Spring Time Outdoor Adventures for Kids: Monday Afternoon’s in the Hilltowns

Registration Form

Outdoor Adventures for Kids in the Hilltowns
Spring 08 Afternoon Program

A nine week Monday afternoon (4pm-5pm) adventure program for kids ages 5-7 at the TMO Base Camp in Chesterfield, MA, starting April 7th and ending June 16th, 2008. Led by Program Coordinator, Timothy Vogel of Tekoa Mountain Outdoors.


Through age appropriate activities, young kids will explore their surrounding environment on foot and in a canoe while learning about ecology through outdoor adventures and activities. This nine week program will lead young Adventurers into the discoveries of spring while experiencing hikes, fishing and canoeing around the scenic 500 acre Base Camp in Chesterfield, MA. As spring arrives, bringing us April Showers, our young Adventures will explore vernal pools as the peepers emerge, make rain sticks to celebrate the season and hunt for insects. In May our young Adventures will go fishing while learning about fish habitat and local wildflowers and plants. And as we approach the summer months we’ll bring out the canoes and learn the basics of paddling and canoe safety. Our last day will conclude with a make-your-own ice cream social by using a tin can! Participants are asked to dress for the weather.


April 7th, 14th & 28th

Week 1 – Monday (04/07/08 )

We will be starting off our spring session by making Rain Sticks and sharing their origins. Our young Adventurers will make a traditional Rain Stick out of materials found in their environment, and like people of other cultures, imitate the sound of rain. Having originated in South America and attributed to many cultures, the Rain Stick is a tubular rattle that has been used by many diverse cultures in various ways and played by children throughout the world.

Week 2 – Monday (04/14/08 )

As spring slowly arrives, our young Adventurers will trek down to the stream to explore our streams and surrounding areas. And there’s more than meets the eye! Upon closer look, we’ll identify different aquatic insects, animals and plants while discussing their importance to our ecosystem. Please bring shoes that can get wet and a change of clothes. Magnifying glass and reptile/insect ID books would be handy too.

Week 3 – Monday (04/28/08 )

As their environment warms up, insects begin to emerge. We’ll identify bugs that fly, swim, crawl and even slither near our watershed while learning their value to our environment. Our young Adventurers will explore under logs and rocks while discovering which insects are useful and which ones we should avoid. We’ll also discuss how to keep ourselves safe from tick and mosquito bites while being adventurous outdoors. Please bring shoes that can get wet and a change of clothes. Magnifying glass and insect ID books would be handy too.

May 5th, 12th, & 19th

Week 4 – Monday (05/05/08 )

We are fortunate to have a rich resource of fish habitat in Western Massachusetts. For the next two weeks our young Adventurers will discover respectful fishing practices. We will learn about tying knots and casting a line while taking a look at different types of bait. We’ll also be discussing hook safety and fish habitat. Fishing poles and gear will be provided. Participants are welcome to bring their own poles too.

Week 5 – Monday (05/12/08 )

We’ll continue our fish explorations as our young Adventurers are introduced to the TMO/MA Angler Education Program. We will continue with learning the basics of fishing, simple biology, fish habitat, fishing gear safety, and courteous fishing habits while instilling respect for fish and their environment. Fishing poles and gear will be provided. Participants are welcome to bring their own poles too.

Week 6 – Monday (05/19/08 )

April shower’s bring May flowers, including Dutchman’s Britches, Trillium, Yellow Violets, and Trout Lilly’s. May is an excellent time to identify wildflowers, plants and trees while discussing how we can avoid poisonous plants while being adventurous outdoors. We will hike around the 500 acre Base camp, and see what April showers have helped to bring to life while discussing their importance to our ecosystem. Participants are welcome to bring along a plant press and ID books.

June 2nd, 9th, & 16th

Week 7 – Monday (06/02/08 )

Our young Adventurers will take to the water for the next two weeks. We will access the waters here at the Base Camp and learn safety skills around the water and canoes. Wearing provided personal flotation devices (PFD), we’ll learn all the different paddle strokes and proper techniques while paddling around our beautiful 60 acre wild and scenic Scout Pond. Please bring shoes that can get wet and a change of clothes.

Week 8 – Monday (06/09/08 )

Our young Adventurers will conclude their canoeing experience, beginning where we left off last week. Wearing provided personal flotation devices (PFD), we’ll continue to practice our canoeing techniques and safety skills as we explore our watershed on canoe. Please bring shoes that can get wet and a change of clothes.

Week 9 – (06/16/08 )

Our last day will conclude our Hilltown Families Spring 08 Program with our young Adventurers playing outdoor games and making their own ice cream by using a tin can! They will learn how to construct their homemade ice cream maker from materials brought from home and follow through by making their very own to enjoy. And ice cream social will follow.


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