Massachusetts isn't the first state that comes to mind for hiking, but the Berkshires in the western part of the state make a genuine case. Bash Bish Falls is the most dramatic waterfall in the state, dropping 60 feet into a granite gorge on the New York border. Alander Mountain above the falls gives a full Hudson Valley panorama from an open summit plateau. Mount Holyoke in the Pioneer Valley has the most historically significant view in New England. Thomas Cole painted it in 1836.
The Berkshire ridge system is anchored by the Appalachian Trail on the Taconic crest and the Metacomet-Monadnock Trail on the traprock ridges further east. Beartown State Forest and the Benedict Pond area offer quieter hiking through rolling second-growth forest that feels surprisingly wild for being an hour from Springfield.
High Rock Fire Tower on South Savage Mountain sits just over the Maryland line but is most easily accessed from the western Massachusetts side — a short hike with surprisingly long Appalachian ridge views. The Worcester Range peaks in central Vermont are accessible day trips from western Massachusetts for those who want more vertical.
Mount Holyoke deserves its own mention. The oxbow of the Connecticut River visible from the summit, the meander bend that Cole made famous in his 1836 painting "The Oxbow" — is one of those views where knowing the history amplifies the experience. The hike is modest (3.2 miles) but the viewpoint is exceptional.
Best Time to Hike in Massachusetts
October for Berkshire color — the ridges west of the Pioneer Valley typically peak in the second week of October. Bash Bish Falls is best in spring (April-May) when water volume is highest. The Berkshires are relatively accessible year-round, though the traprock ridges can be icy in winter.
Frequently Asked Questions
Is Bash Bish Falls worth visiting? Yes. It's the most impressive waterfall in the state and the gorge setting is beautiful even outside of peak flow. Combine it with Alander Mountain for a full day.
Is hiking in the Berkshires free? Most state forest trails are free. Bash Bish Falls is in Taconic State Park — free parking on the New York side, small fee on the Massachusetts side.
What is the best hike in Massachusetts? Bash Bish Falls combined with Alander Mountain is the strongest full-day option in the state. Mount Holyoke is worth including if you're in the Pioneer Valley.
