Kayaking in Winchester Center

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Westfield Water Sports and Wilderness Experiences—a kayak, SUP, camping, and scuba gear shop as well as a camping store and adventure emporium—dispatches a staff of certifiable adventure-seekers to lead sojourners into the great outdoors with scuba classes, kayak classes, dive and non-dive world travel, and rock-climbing excursions. An all-around outdoorsman, camp director T. Scott Cook leans on his doctorate of Leadership Development in Adventure Education to develop nature excursions, including far-flung trips where groups snorkel in the Cayman Islands or evolve gills in the Galapagos. Back home, the summer camp’s elaborate ropes course builds teamwork between coworkers, and caving adventures allow guests to delve into mysterious depths or apartment swap with a black bear.

526 College Hwy
Southwick,
MA
US

The merry mariners at H. P. Kayak & Boat Rentals provide prospective paddlers with a fleet of colorful crafts to explore the Connecticut River. Before your two-hour tour, choose to fly solo in a single-person kayak (a $30 value) or tote along co-pilots in a rowboat (a $35 value), dual-passenger kayak (a $35 value), or two-person canoe (a $35 value). Then push off shore and seize the open water, where you'll behold a real-life viewfinder's worth of scenic wildlife, including eagles and Frisbees, while advancing oarsmanship, teambuilding skills, and general awareness of water.

684 Tryon Street
Glastonbury,
CT
US

Visitors of all ages can learn to skate, twirl across the ice, and handle pucks at Northford Ice Pavilion, where they will find a variety of frozen activities for the whole family. Boys and girls as young as aged 3 can enroll in hockey sessions that run eight weeks and involve supervised practice, group lessons, and building shrines to Wayne Gretzky. Open skate welcomes kids, parents, and couples to glide on rented skates before enjoying a hot cocoa at the concession stand.

24 Firelite Place
Northford,
CT
US

From rock climbing, to kayaking, to camping, Tekoa Mountain Outdoors' founder Tim Vogel views the great outdoors as a combination of playground and classroom, a place where adults and children can learn by doing. Tim has been teaching and guiding adventure activities for more than 25 years, and his experience aids him as he plans adventurous exhibitions, such as hiking along the Appalachian Trail or searching for lost car keys in the Wards Gregory Cave System. During outings, Tim teaches his students both introductory and advanced techniques. Along with a team of certified guides, Tim advocates passion for the outdoors and love for every blade of glass, even the stubby crab variety. In addition to working with the Boy Scouts and Girl Scouts of America, the staff leads several education programs that teach youth valuable team-building lessons. They also run the WOLF Program, which cultivates new crops of professional leaders within the expedition and adventure industry.

27 Sugar Hill Road
Williamsburg,
MA
US

The instructors at EMS Schools traverse rocky, paved, and watery terrain from New England down to Virginia, imparting people with their love of the outdoors along the way. Dating back more than 40 years, the EMS Climbing School teaches pupils of all ages the tenets of climbing through introductory classes and more advanced maneuvering in self-rescue, alpine climbing, and glacier-skills classes. The watery wing of EMS's operation includes kayaking and standup-paddleboard lessons, which can help students earn certification in these water-bound endeavors, and group tours. EMS-led bike tours trace a path through the rolling hills of the Berkshires, the mansions of Newport, as well as the powdered-sugar-topped White Mountains of New Hampshire.

3124 Route 44
Gardiner,
NY
US

In Jack Kerouac’s On the Road, narrator Sal Paradise has this to say about New York’s most famous river: "If you drop a rose in the Hudson River at its mysterious source in the Adirondacks, think of all the places it journeys by as it goes out to sea forever—think of that wonderful Hudson Valley." At Mountain Valley Guides, the kayaking team allows customers to heed Sal’s thoughts and explore the river's expanse of open water, marshes, islands, and cliffs.

2 Idlewild Avenue
Cornwall On Hudson,
NY
US