Top 3 Weekend Hiking Getaways in New England

There’s something for every adventurer in New England—verdant valleys, roller-coaster ridges, crystal cascades, acres of wildflowers, 17th-century villages—and almost all of it is conveniently located within a day’s drive of Boston, the region’s largest city and air hub. Here you can chase a good day’s hike with a bowl of lobster stew, a mug of locally brewed dunkelweizen, or a performance by an outdoor puppet circus famous for its civil rights-era activism. Whatever your preference, there’s a hiking getaway for you—here are 3 perfect itineraries for a long weekend spent soaking up the great outdoors.

Long Strange Coast

Experience the magic of the northern New England seacoast in two nights and three days.

Jewell Falls
Jewell Falls, the only naturally occurring waterfall in Portland. Photo © Miles Howard.

DAY 1:
Start your expedition by admiring the ecological diversity of New Hampshire along the Sweet Trail. From there, head north to Portland, Maine, to explore the city’s renowned food and nightlife circuit and spend the night.
DAY 2:
In the morning, take a jaunt over to the city forest and hike to Fore River and Jewell Falls. Then jump on US-1, grab a bite to eat at any of the lobster and clam shacks near Wiscasset, and continue north to Rockport for an afternoon climb up Ragged Mountain. Decamp in nearby Rockland or Belfast for dinner, drinks, and lodging.
DAY 3:
Wake up early the next morning, enjoy a nice local breakfast, and make your way to nearby Camden Hills State Park and climb Mount Megunticook for a final ocean vista. If you find yourself pining for the beauty of the seacoast as you begin the journey home, stop by Wells Reserve or Odiorne Point State Park for a lush, meditative stroll alongside the Atlantic before it’s time to hang up your boots.

Alpine Trilogy

Challenge yourself to three mountain summits in three New England states in three days!

Hiker holding beer
Photo © Long Trail Brewing/John Lundquist.

DAY 1:
Get a good night’s sleep and rise at dawn to drive north through the greenery of Vermont to Camel’s Hump (aim to summit before 2pm). Balance the adrenaline rush with a hearty locally sourced dinner and a few craft beers in Montpelier, and spend the night in Vermont’s capital.
DAY 2:
Get up early the next morning and head east into New Hampshire where— depending on how tired you are after yesterday’s formidable ascent—you can work your way up the moderately difficult Welch and Dickey, or the easier and shorter Mount Willard. Knock both off if you feel like it! Then drive to either North Conway or Gorham for another round of decadent cooking and craft libations. But don’t stay up too late. You’ll finish big on day 3.
DAY 3:
For on the third and final day, you’ll drive north across the Maine border and climb the mighty Old Speck—one of the most thrilling hikes in this book. At least, that’s the ideal finale. If you’re feeling beat after two days of summits, you can easily swap Old Speck for Mount Agamenticus on Maine’s southwestern oceanside, a two-hour drive from the White Mountains.

Island Hopper

Hike three of New England’s scenic offshore islands on this easygoing tour around the Atlantic seaboard.

Sunset at Sandy Neck
Sunset at the Sandy Neck dunes. Photo © Kelsey Perrett.

DAY 1:
Head east through Massachusetts and cross over the bridged canal marking your arrival in idyllic Cape Cod. Park at the Steamship Authority lot in Hyannis and enjoy a leisurely ferry ride to Nantucket. Take a bus or taxi a few minutes outside Nantucket town to explore the varied local terrain at Sanford Farm, Ram Pasture, and The Woods. Stay and play on the island, or hop back on the ferry to spend the night in Hyannis.
DAY 2:
Wake up and drive approximately 25 miles southwest to Woods Hole, where you can pick up the Steamship Authority ferry to Martha’s Vineyard. From either Vineyard Haven or Oak Bluffs, where the ferries drop off, catch a ride to pastoral Chilmark, about 15 miles away, and spend some time admiring the sweeping ocean views at Menemsha Hills Reservation. Treat yourself to a night on the Vineyard, or return to Falmouth for dinner and a good night’s sleep.
DAY 3:
Get up early to beat the Cape Cod traffic and get a jump on your 2-hour (85 miles) drive to Rhode Island. From Falmouth, make your way west around Buzzards Bay. After a scenic crossing of Narragansett Bay, you’ll arrive in Narragansett, where the ferry to Block Island departs. The pleasant ferry cruise will deliver you just a few minute’s drive from Clay Head Preserve, an easy walk around the beach and the imposing clay cliffs of Block Island.

Kelsey Perrett

About the Author

Miles Howard grew up in Massachusetts, where he and his family headed north to the mountains every summer. As a young hiker and later, a live-in caretaker and staff manager for the Appalachian Mountain Club’s wilderness hut system, he honed his love for the great outdoors. Any given day on the job as a professional mountain man could have involved dispensing trail advice, cooking a five-course meal for 60 people, or immobilizing a broken leg. In his spare time, he would toss a few Snickers bars in a bag and explore the landscape by foot.

He eventually traded his hiking boots for hi-tops and moved to Boston, where he wrote for the Boston Phoenix and eventually launched a freelance career. Along the way, he also researched and wrote his first book: a study of Millennial-aged adults in America, their political beliefs, and their thoughts on the 2016 US election.

Miles still lives in Boston today, but takes every chance he gets to return to the New England wilderness he calls home.

Kelsey Perrett grew up in north central Massachusetts, in the shadows of Mount Wachusett and Mount Watatic. It was there that she developed an admiration for New England’s steep rugged trails and bald granite faces, and a passion for backpacking, trail running, and wilderness medicine. She eventually traveled across the country (and others!) to bag peaks and seek out scenic vistas, but returned to where she felt most at home: performing trail work with the Appalachian Mountain Club in the Berkshires and White Mountains.

She honed her writing career at New England’s Yankee Magazine, and wrote for publications like and, where she is still a contributing editor. Kelsey holds a Wilderness First Responder certification and a trainer certification from the Leave No Trace Center for Outdoor Ethics, among other environmental credentials. She lives in Boston.

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Miles Howard

About the Author

Having grown up in New England, Miles Howard is no stranger to the art of road tripping, from family treks to northern Vermont (to hunt for Christmas trees) and the islands of Midcoast Maine (to escape the tourist mobs). But in 2016, after multiple cross-country road trips, he found himself with a renewed passion for digging deeper into the New England landscape and its communities. He began writing about travel in his regional home—with lots of field research trips, of course.
Since then, he's covered New England travel with an eye for the peculiar and sublime—including charting the most beautiful trails of Maine, New Hampshire and Vermont—and the best breweries—for his first travel guide, Moon New England Hiking. He traveled from Pittsfield to Provincetown using only municipal transportation and wrote about the adventure for Boston Magazine. He’s also written for Boston Magazine, The Boston Globe, Southwest Airlines: The Magazine, and others.

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