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Posted by Katie Marshall, guest blogger of The Trustees of Reservations

Back in May, The Trustees began celebrating its 125th anniversary as the world’s first land preservation nonprofit with free and ticketed events and programs across the state, like the Boston Pops Esplanade Orchestra’s first-ever concert at Castle Hill on the Crane Estate, free property entry days, and more. We also saw this milestone as an opportunity to inspire Massachusetts residents and visitors to get out, get active, and explore the natural splendor of the state through our Hike 125 challenge, and share their experiences with us! Since the challenge began, over 1,100 hikers have taken more than 3,500 hikes and logged over 12,000 miles on Trustees properties and have been entered to win prizes from Trustees partner REI Co-Op like tents, sleeping bags, backpacks, binoculars and other great outdoor recreational items.
With the holidays approaching and great fall weather still in full force with crisp air, foliage, and beautiful vistas to explore, it’s not too late to join the Hike 125 challenge. Just log on and create your hiker handle and get started at Now through New Year’s Eve, gather family and friends and chose from 116 scenic, natural, and cultural Trustees properties. After each hike, submit your miles and enter to win prizes for your miles hiked in increments of 25, 50, 75, 100 and, of course, 125 miles! Prizes also include a stay at Trustees properties and Trustees memberships and merchandise.
Not sure where to start? Here are some of our favorite hikes across the state, with something for everyone and all fitness levels.  And on “Green Friday,” the day after Thanksgiving, Trustees properties that are normally gated or charge parking fees are free and open to all who chose to join us and support REI’s call to forgo shopping and #optoutside.

For great views

Monument Mountain in Great Barrington, inspiration to legendary authors Herman Melville and Nathanial Hawthorne and is best for experienced hikers. Peaked Mountain in Monson has views stretching to Vermont and Pegan Hill sports the highest point in Natick offering a panoramic view of Mount Monadnock and Mount Waschuset.

Monument Mountain | massvacation.comMonument Mountain, Great Barrington

For those who’d prefer a gentle pace

Francis William Bird Park in Walpole has three miles of flat pathways, grass meadows and tranquil ponds. Field Farm in Williamstown is nestled on a Berkshires hillside with a beautiful view of Mount Greylock and four miles of gentle, meandering trails as well as a unique, 10-room bed and breakfast still open on weekends through December with décor straight out of Mad Men, the Guest House at Field Farm for some R&R.

Francis William Bird Park | massvacation.comFrancis William Bird Park, Walpole

For those with tots in tow

Picturesque Appleton Farms and Grass Rides in Ipswich has five miles of walking trails originally designed for a horse and carriage, so nice and smooth for strollers. In Medfield, Rocky Wood’s two hundred year old logging roads are easy going for little ones. Take the Bridle trail across the footbridge at Echo Pond to see lots of beaver activity!

Appleton Farms | massvacation.comAppleton Farms and Grass Rides, Ipswich

Historic hikes

It’s hard to believe that Norris Reservation in Norwell was once part of America’s first shipbuilding center. The Beaver, of Boston Tea Party fame, was launched here! Now you can walk through quiet white pine and oak forests along the tidal North River. At Whitney and Thayer Woods, in Hingham and Cohasset, you’ll walk to carriage roads to panoramic views of the Boston Harbor atop Turkey Hill, the vantage point where townspeople watched the War of 1812. 

Whitney and Thayer Woods | massvacation.comWhitney and Thayer Woods, Hingham & Cohasset

All photos credit of The Trustees of Reservations