What’s more quintessentially Maine than lobster, L.L.Bean, and a placid, fog-drenched bay dotted with islands? Just bring Thoreau’s Walden and you’ll reach nor’east nirvana on L.L.Bean’s Casco Bay paddling expeditions. The inlet’s uninhabited, pine-clad isles host a series of three-day, two-night camping trips in August and September ($475; llbean.com). By day, paddle slaloms in tandem kayaks around frisky seals and lobster buoys while ospreys and gulls soar overhead. First stop is Eagle Island, once owned by Arctic explorer Robert Peary (his home there is now a museum). Evenings are spent lolling on Bean’s private island base camp, feasting on lobster and a traditional New England clambake. And if you happen to need a piece of gear for the trip, you can guess where to pick it up: The sporting mecca is open 24 hours.
Zoar Outdoor guarantees paddlers will be satisfyingly exhausted at the end of a weekend of whitewater kayak lessons on the Class II Deerfield River in the Berkshires of western Mass ($275; zoaroutdoor.com). “You’ll work hard physically and mentally,” says owner Karen Blom. “Our instructors encourage you to push your limits—which means a lot of flipping your boat and swimming it to shore, getting very wet and tired.” But by the second day you’re applying what strokes you’ve learned on ten miles of river. At day’s end, roll out of your kayak and into Zoar’s own Hawk Mountain Lodge ($75; hawkmountainlodge.com).
Realistically, most of us will not be coaxing our creek boats over 18-foot Ohiopyle Falls on August 23 during the Ohiopyle Over the Falls Festival in Ohiopyle State Park (fallsrace.com). For whitewater athletes, it’s the rare chance to run a drop on the Youghiogheny that’s normally off-limits. The rest of us can watch from the Falls Day Use Area and find plenty to do in Ohiopyle State Park’s 19,052 acres. The wildland is home to walk-in tent sites ($13), the Class IV Lower Yough (below the falls), 27 miles of the Yough-iogheny River Trail for easy biking, and 9.4 miles of more challenging trails in the Sugarloaf Snowmobile and Mountain Bike Area.
Ontario’s 500-mile Bruce Trail is the longest (and oldest) footpath in Canada, stretching from near Niagara Falls to Tobermory on the Bruce Peninsula in Georgian Bay (brucetrail.org). For an epic three-day taste, hike 24 miles from Dyer Bay to Cape Chin south to Lion’s Head. This northern section, about three hours northeast of Toronto, showcases Niagara Escarpment scenery at its finest: sheer dolostone cliffs plunging into blue-green waters, sea caves, and cobble beaches (terraced slabs of limestone) made for a nosh break. Plus, the whole peninsula is a "dark skies" community, so the Milky Way is always on display. Cape Chin Connection Country Inn serves up big breakfasts, provides a sack lunch, and arranges shuttles to and from trailheads ($95; capechin.ca/capechinconnection.html).