Adventure Itinerary
ADVENTURE: 14-Day Itinerary
This trip leaves no room for boredom: Climb Maine’s highest mountain on one end, dive with sharks off Cape Cod on the other. In between? As much hiking, paddling, fishing, sailing, and exploring as you could wish for.
DAYS 1 & 2: MAINE
Learn more about visiting Maine
Lodging ideas: AMC wilderness lodges (Medawisla, Little Lyford, and Gorman Chairback—Greenville), New England Outdoor Center (Millinocket), North Country Rivers (Bingham), Snow Cap Inn (Newry)
The 87,500-acre Katahdin Woods and Waters National Monument is the Northeast’s only designated Dark Sky Sanctuary thanks to its exceptionally starry nights. By day, it offers over 50 miles of hiking trails, gravel roads for mountain biking, and rivers teeming with fish. The monument borders Baxter State Park, home to the nearly 5,300-foot Mount Katahdin. Climbing Maine’s highest peak can take up to 12 hours round-trip, but the view is worth it.
Some of the most thrilling whitewater rafting in the country can be found on Maine’s “big three”: the Penobscot, the Kennebec, and the Dead rivers. The sport’s epicenter is the Kennebec Valley, where outfitters like North Country Rivers lead expeditions through class III-V whitewater. Those who prefer more leisurely water adventures can book guided fly-fishing trips throughout the state with NaviTour, or paddle at their own pace at spots like Moosehead Lake or on the Maine Island Trail or Northern Forest Canoe Trail.
DAYS 3-5: NEW HAMPSHIRE
Learn more about visiting New Hampshire
Lodging ideas: AMC Highland Center (Bretton Woods), AMC Joe Dodge Lodge (Gorham), Lopstick (Pittsburg), Tall Timber Lodge (Pittsburg)
Sitting below the fabled Presidential mountain range, the AMC Highland Center offers guests easy access to several popular White Mountain hikes—self-guided or led by AMC staff—and can even loan them equipment for their trek, from boots to backpacks.
Hop on an ATV to explore New Hampshire’s most remote and wild region, the Great North Woods, on the 1,000-mile-plus Ride the Wilds trail system. Bear Rock Adventures in Pittsburg offers ATV rentals; add an overnight in a glamping tent with its “Stay and Play” package. Or book a stay at Pittsburg’s Tall Timber Lodge or Lopstick and take advantage of the on-staff fishing and hunting guides. Fly-fishing fans won’t want to miss a chance to try the mighty Connecticut River nearby.
Another Great North Woods standout is Umbagog Lake, one of the best paddling destinations in the East. The 11-mile-long lake and the adjacent Umbagog Lake State Park and Umbagog National Wildlife Refuge are home to loons, eagles, ospreys, moose, and myriad species of northern freshwater fish.
DAYS 6 & 7: VERMONT
Learn more about visiting Vermont
Lodging ideas: Hotel Jay (Jay), Killington Mountain Lodge (Killington), Lake Morey Resort (Fairlee), Mountain Meadows Lodge (Killington), Phineas Swann Inn & Spa (Montgomery), Sterling Ridge Resort (Jeffersonville)
New England’s only landlocked state is not short on water adventures. It’s known for superb swimming holes, and the Northeast Kingdom region has some of the best, including Montgomery’s Three Holes, named for its three waterfalls, and Four Corners in North Troy, with diving cliffs and a thrilling rope swing. Or take a guided paddle tour of the Northeast Kingdom’s Clyde River, a gentle waterway with abundant wildlife, with Clyde River Recreation. Before departing the Kingdom, stop by Hill Farmstead Brewery to taste beers that many consider to be the world’s best.
The big ski mountain Killington keeps outdoor lovers’ adrenaline pumping all year round. Tackle the 4.1-mile Killington Peak loop trail to the summit or rent a mountain bike and explore 30-plus miles of trails at the Killington Bike Park. You can even try your hand at rock climbing with Killington Mountain Guides—then reward yourself with a pint or two at Long Trail Brewing Company, named for Vermont’s 273-mile hiking path that inspired the Appalachian Trail.
DAYS 8 & 9: CONNECTICUT
Learn more about visiting Connecticut
Lodging ideas: Heritage Hotel (Southbury), Hotel Zero Degrees (Danbury), The Watershed (Norwalk), Winvian Farm (Morris)
Let your Connecticut thrill-seeking begin with an early-morning ride with New Hartford’s Berkshire Balloons, as you float high into the sky and enjoy unforgettable views of up to 100 miles. Then head into the rolling Litchfield Hills for more down-to-earth adventures. Feel the thunder of race cars at Lime Rock Park, which also hosts occasional driving experiences by Skip Barber Racing School for budding speed demons. Or climb into a rugged off-road vehicle for a guided outing with Backyard Adventure UTV Tours, whose private trails traverse woods, fields, and (if you’re lucky) mud.
Round things out on a quieter note with a Litchfield Hills fishing expedition: At the 113-acre luxury resort Winvian Farm, guests can embark on guided fly-fishing or spin-casting trips or borrow gear to head out on their own.
DAYS 10-12: RHODE ISLAND
Learn more about visiting Rhode Island
Lodging ideas: Block Island Beach House (Block Island), The Break Hotel (Narragansett), Hammetts Hotel (Newport), Hotel Manisses (Block Island)
The waters off Block Island offer some of New England’s finest saltwater fishing. Get an early start with a Block Island Fishworks charter and spend the next four to six hours pursuing striped bass, bluefish, and more. For more on-the-water action, book a private sailing lesson with the Block Island Club on the Great Salt Pond.
Few visitors to Block Island know its history as a settling point as early as 500 B.C. for the Niantic tribe, who called the island “Manisses.” Researchers from the University of Rhode Island have worked to bring that history to light with the Manissean Walking Tour. You can also plot your own course around the island, hiking as few as two miles around the Old Harbor or as many as 15, to encompass historic lighthouses and the famous Mohegan Bluffs. Afterward, wind down with ocean-view cocktails on the veranda of the Atlantic Inn.
Back on the mainland, catch a wave in the surfing town of Narragansett, where outfitters like Warm Winds and Narragansett Surf and Skate offer rentals and lessons. In nearby Point Judith, the Frances Fleet has whale-watching excursions and fishing trips that include night fishing for squid. Paddling aficionados should stop into Narrow River Kayaks for kayak, canoe, and paddleboard rentals, as well as ideas on where to take them (naturally, the company’s scenic namesake is a favorite).
Finally, head to Newport for a one-hour “Try Sailing” lesson with the community sailing center Sail Newport, and see this legendary yachting capital in the most fitting way possible.
DAYS 13 & 14: CAPE COD, MASSACHUSETTS
Learn more about visiting Massachusetts
Lodging ideas: Harbor Hotel (Provincetown), Blue Water Resort (South Yarmouth), Red Jacket Beach Resort (South Yarmouth), Cape Codder Resort & Spa (Hyannis)
Feel the thrill of sinking that perfect putt on Massachusetts’s “Golf Coast,” as Cape Cod challenges golfers of all abilities with some 50 courses, most of them public. Among the standouts are Truro’s Highland Links, the Cape’s oldest course, and Captain’s Golf Course in Brewster, home to two par-72 championship courses.
For a less expected adventure, stop by the Cape Cod Airfield for a biplane ride; book a shark dive with Bounty Hunter Shark Adventures or Cape Cod Shark Diving; or take a guided off-road expedition into the Cape Cod National Seashore with Art’s Dune Tours. And, given Cape Cod’s proximity to prime feeding grounds for humpbacks, minkes, and other whales, be sure to make time for a whale-watching trip with Dolphin Fleet or a private outing with SeaSalt Charters.
Itinerary created in partnership with Yankee Publishing. DATTCO Coach & Tour is Discover New England’s transportation partner.
