By Sandi Barrett
Contributing Writer
REGION – Fallen leaves crackling with each footfall, chilly temperatures invigorating your lungs, while a backdrop of pine forest, maple groves, and expansive meadows are reflected on glasslike ponds along the way. Fall and early winter hiking is a wonderful way to enjoy the outdoors.
Massachusetts offers residents an extensive park system where you can partake in easy hikes along gentle, rolling pathways. As a Massachusetts resident over 62, you can purchase a lifetime state park parking pass for only $10. This pass covers free parking for one vehicle at most Department of Conservation and Recreation facilities. Apply at Mass.gov Senior Parking Pass Guide (https://www.mass.gov/how-to/get-a-senior-parking-pass). Alternatively, you can borrow a day-pass from your local library. Better deal than any gym membership and the fresh air is included.
Below are a few of the many Massachusetts state parks that have easy hiking trails. Most allow dogs on leash and a few have off-leash areas. Visit the park website for hours, parking, and admission fees. Grab your water bottle, a snack, and explore our beautiful Commonwealth.
Bash Bish Falls State Park, Mt. Washington
The falls can be reached by two different paths. The path on the Massachusetts side is a very steep mile and can be challenging. For a longer, 1.5 mile out and back trek and gentle climb, approach from the New York side in Taconic State Park. The reward for your efforts is the beautiful falls. Beware, they are barricaded and inaccessible from the trail, but picturesque, nonetheless.

Callahan State Park, Framingham/Marlborough
Callahan State Park in Framingham and Marlborough offers several flat, wide, and easy walking loops that pass through open fields, quiet woods, and scenic ponds. Easy trails under two miles include Bear Paw, Backpacker, and Pine Tree Loop. For a longer hike consider Eagle Pond Loop, a 3.4-mile loop that winds by Eagle Pond.
Castle Island, Boston
A little unexpected, yet a wonderful spot to spend a sunny day, Castle Island offers visitors a 2.2-mile loop around Pleasant Bay and Fort Independence. It is a popular spot for picnics, casual strolls, and dining at the iconic food stand Sullivan’s Castle Island. This is more like a walk than a hike and is accessible for guests with mobility challenges.

Photo/Sandi Barrett
Massasoit State Park, East Taunton
Trails winding through pine forests and around pretty ponds, Massasoit State Park is a family-friendly destination. Five Pond Loop is a 3-mile picturesque trail with offshoots to the cranberry bogs. Rico Trail is a flat, 2-mile trail along Lake Rico. The namesake trail, Massasoit Loop, is a long, but easy 4-plus mile walk offering forest and water views.
Moore State Park, Paxton
A beautiful hiking destination offering well cared for hiking trails, pretty views, pond, bridge, and waterfall – what more could you want from a walk in the woods? There are currently two trails open, both rated as easy and both under two miles.
Nickerson State Park, Brewster
Hiking in Nickerson State Park is more than passing through on the Cape Cod Rail Trail. There are scenic trails winding through the park with views of ponds, meadows, campgrounds, and forests. Offering mostly flat, sandy trails, the park is a wonderful spot to explore.

Photo/Sandi Barrett
Flax Pond Loop is a very easy, 1.4-mile trail that winds around a kettle pond. Little Cliff Ponds Trail offers slight elevation changes along the 1.6-mile path. The Cliff Pond trail is longer, but a gentler looping 2.4-miles through pine forests and sandy ponds. Higgins Pond Loop is a less traveled 2.2-mile trail, a walk of peaceful contemplation.
Purgatory Chasm State Reservation, Sutton
Best known for rock scrambling and intensive hiking, Purgatory Chasm has an easy trail that affords you a bird’s eye view of the chasm. You won’t be squeezing through and over narrow formations like Fat Man’s Misery, The Corn Crib, The Coffin, or Lover’s Leap, but you will get a one mile walk and a view of the 70-foot-deep gorge. A word of caution, there are no safety rails at the precipice, so it might not be the best hike for young children.
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