The long-ish trails
Get saucy and try a multi-day hike in Southern New England
Is there anything more romantic than a single trail weaving miles and miles across rustic woodlands, wetlands, and peaks? The idea that you can traverse multiple environments and counties by following one path blazed with the same colors or symbols brings to mind the epic journeys we grew up with—Frodo and Sam huffing their way to Mount Doom, Milo and Otis finding their way back to the farm, or those preadolescent dinosaurs searching for the Great Valley in The Land Before Time. I could go on. Nothing underlines the “journey” element of hiking like a trail that takes multiple days and nights to complete. We can’t resist these long trails.
Most of the time, when we think of trails like this, we immediately level up to Godzilla-sized hikes that run for hundreds of miles. The Appalachian Trail passes through five of the six New England states along its 2,190 total miles. Vermont’s Long Trail is a straight shot from the Massachusetts state line to the Canadian border at 273 miles. And while these trails certainly offer the experience of a grueling yet scenic journey, they’re quite a logistical undertaking in one thru-hike or even in sections. Even when you’re able to commit to tackling one of these epic trails, they tend to be fairly busy, given the allure of being the longest trails in the U.S.
Recently, I’ve been hankering for more bite-sized “long-ish trails” that can be finished over 3-5 days. And after a couple of trips to the stacks at the Boston Public Library, I’ve got some exciting news. Southern New England is loaded with long-ish trails.
You could think of a long-ish trail as practice for the more formidable giants up north, but who are we kidding? Hiking double digit miles in one day is rough on your soles. Doing this multiple days in a row—say, over a weekend—can leave you pacing around your workplace gingerly the following Monday morning. You don’t have to thru-hike for hundreds of miles to feel like you’ve accomplished a feat worthy of Tolkien (even if hiking magazines and movies propagate this idea.) And now that we’re heading into the sultrier days of spring, with the mud flowing like wine and little petals opening up, now is the perfect time to consider taking on one of Southern New England’s long-ish trails.
So for your planning purposes, I’ve rounded up four of the most enticing long-ish hikes in Connecticut, Massachusetts, and Rhode Island. These trails run less than 100 miles each, covering a diversity of landscapes that represent the ecology of each state while also offering lots of climbing and scrambling that—in the words of Homer Simpson— will leave you sweating like Roger Ebert. So go forth, bring lots of water, and be sure to perform a thorough tick check after your hike. Those little devils are waking up now…