TRAVEL: 40 MILES
Rent a boat from North Shore KayakOutdoor Center ($20; northshorekayak.com), in Rockport, paddle almost three miles to Thacher Island (thacherisland.org), and climb to the top of one of the twin lighthouses where, on a good day, you can see all the way to Provincetown. Back on the mainland, enjoy the view of Rockport Harbor from an oceanfront deck at the Peg Leg Inn (doubles from $145; thepegleginn.com).
TRAVEL: 75 MILES
Land a suite for the weekend at the Winnetu Oceanside Resort (doubles from $260; winnetu.com), on Martha's Vineyard, then hit the beach with your rod and reel. Try your luck with stripers in the surf at South Beachonly 250 yards from your dooror bike over to Menemsha and fly-fish for albacore.
TRAVEL: 89 MILES
Roll over 15 miles of new and refurbished singletrack inside central Massachusetts's Wendell State Forest. The three-mile Hannah Swarton Trail skirts past rock ledges and laurel thickets and down switchbacks (mass.gov/dcr/parks/central/wndl.htm). At the end of the day, quench your thirst with a Red-Headed Stepchild at the Northampton Brewery Bar and Grille before heading to the nearby Hotel Northampton (doubles from $175; hotelnorthampton.com).
TRAVEL: 189 MILES
Work your legs in Maine's Mahoosuc Mountains on the new 13-mile addition to the Grafton Loop Trail (matc.org/glt1). Unveiled this summer, it traverses some of the most rugged and, until now, inaccessible land in the state. Follow the Appalachian Trail from Grafton Notch State Park and climb up 4,180-foot Old Speck, the third-highest mountain in Maine, then connect with the GLT and make your way up to Sunday River Whitecap for one of the best views of the Mahoosucs. With 39 miles of trails and eight campsites in the area, multi-day adventures abound, but after a long day you may crave a little TLC, so make tracks to the spa at Sunday River Resort (doubles from $115; sundayriver.com).