Chelmsford, MA Outdoor Activities

While the 90-foot long Thomas E. Lannon schooner boasts many impressive characteristics—including a 64.5-foot deck, a spacious 18-foot beam, and a resemblance to a 1903 sword-fishing schooner—none of them rivals the story of how the vessel got its name.

Before the ship was built in 1997, owner Tom Ellis was visiting his relatives in Newfoundland when he overhead them reciting stories of his grandfather Thomas Lannon, who had fished the Gloucester coastline for more than 40 years. On one particularly stormy day in 1908, Lannon and five other men set out into the waters off Nauset aboard two dories and rescued the crew of the capsized schooner Eric amid 70-mph winds. Each of the rescuers received the eternal admiration of the rescued men and a medal from the Massachusetts Humane Society, which Ellis possesses to this day.

More than a century later, the crew of the Thomas E. Lannon keeps its namesake's love of the sea alive by chartering an array of sailing voyages that have attracted more than 100,000 passengers to date. After helping raise the sails at the voyage’s start, passengers capture vivid views of Gloucester harbor's lighthouses, castles, beaches, and waterfront homes sold by Poseidon himself.

At Skydive Pepperell, USPA– and state-licensed and certified instructors acquaint adventurers with the thrill of riding gravity back to the earth's crust. Skydive Pepperell's private, skydiving-only airport claims more than 60 acres for soaring steel birds at heights of 10,500–13,500 feet above ground. Neophyte fliers, harnessed to professionals for tandem jumps, leap from the belly of a DeHavilland DHC-6 Twin Otter and indulge in trendy cloud diets on their way down to the safe, grassy landing area. Daredevils who thrive on the thrum of adrenaline can enroll in accelerated free-fall training, which drills students in the skills necessary for a solo dive. Jumpers can also purchase a DVD and digital stills that show them soaring through the sky while demonstrating ways to repurpose a parachute into a giant stuffed animal. Meanwhile, spectators watch jumps from the open landing area, confident in Skydive Pepperell's impeccable safety record.

Surrounding Kennebunkport Marina is a town awash in centuries of nautical history; the community also boasts a spot on AOL Travel's list of the 10 Best Beach Towns in America. The marina contributes to its pristine environs with new docks, an outdoor fireplace, and a riverside courtyard where guests can lounge on adirondack chairs. From the docks, which have hookups for water and 30- and 50-amp service, boaters can captain their vessels down the Kennebunk River or travel one-quarter mile to open ocean waters. Year-round storage keeps ships protected during winter or transatlantic spitball wars, and spring engine commissions by certified technicians prep boats for the sailing season.

Those without their own watercraft can join the Kennebunkport Boat Club, which grants members of any skill level access to a quartet of boats that range from 15 to 26 feet. Additionally, the store offers powerboat, canoe, and kayak rentals, and reservations of the Captain's Cottage make lodgers feel more nautical than tying their shoelaces in bowline knots.

A coach at the first Equine Special Olympics in 1999 and again in 2011, North American Riding for the Handicapped–certified trainer Kathleen Gallant possesses a deep, long-lasting love for horses and their ability to help others. After attending equestrian vocational school as a teenager and working at several race tracks, Kathleen developed her passion for jumping and dressage and began teaching others, which she has been doing for more than two decades. Today, English riding lessons are the focus at Chiron Equestrian Services, as well as therapeutic riding for children and adults with special needs. Both private and group lessons begin with the establishment of a balanced, centered riding style and, once these basics are mastered, move on to more advanced riding techniques such as hunt seat, jumping, and dressage.