Cheshire, CT Outdoor Activities
Outdoor Activity Deals
Cycle Evolution RealRyder Fitness Studio
- East Islip
Full-body workouts atop RealRyder indoor cycles that tilt, turn, and lean much like real bikes
Extreme Paintball Hartford, CT
- Waterbury
Six paintball fields stretch across 50 acres and are monitored by refs to ensure safe paintball excursions
Woodbury Ski Area
- Woodbury
Visitors enjoy warm-weather activities such as swimming, tubing, ziplining, or rolling down a mountain inside a giant inflatable sphere
Vintage Bicycle Tours
Guides lead approximately five-hour, 12-mile tour through Long Island wine country, including stops at wineries for eight total tastings
Rusty Wallace Racing Experience
- Stafford Springs
Professional drivers sate passengers' need for speed in stock cars during exciting ride-alongs and racing experiences
Spins Bowl Grand Prix New York
- Mount Kisco
Adults, kids, and teenagers race around go-kart tracks at speeds of up to 40 mph, then go head to head in the video-game arcade
Centennial Golf Club
- Carmel Hamlet
27-hole championship course leads golfers across a multitude of landscapes as they make their way over hilly fairways with lush greenery
Schooner Inc
- Hill
Explore the Long Island Sound with the Quinnipiack schooner’s captain and crew for an educational trip, BYOB cruise, or private charter
Stone Age Rock Gym
- Manchester
Climbers learn the basics during an instruction course before taking on walls aided by a suite of rented gear
Wings Air
- White Plains
Tours provide aerial views of NYC sights; private pilot experiences let students try their hand at flying helicopters themselves
Long Island's Laser Bounce
- Levittown
Multifaceted complex fosters friendly competition in laser tag, bounce arena, and Ballocity arena
Mark's Tree Farm
- Hebron
High-powered laser pointer and large telescope showcase planets, galaxies, and nebulae during guided astronomy tour
The Rock Club
- New Rochelle
Staffers help climbers learn beginner rock-climbing skills to prepare them for one month of faux rock scaling
CharterMySeaRay.com
- South Norwalk
Coast Guard–certified captains man boats around scenic Norwalk Harbor while passengers sip champagne and snack on cheese and crackers
The Cliffs at Valhalla
- Briarcliff Manor
Certified instructors teach knot tying, harness use, and belay techniques before climbers practice on 13,000+ square feet of indoor terrain
Seascapes USA
- Syosset
PADI-certified instructors teach aspiring aquanauts basics of scuba diving in heated indoor pool and provide all necessary gear
Island Rock
- Plainview
Students learn the proper climbing form and how to belay before taking to 30-foot climbing walls or a 25-foot rappel tower
Capt. Saam's Scuba School
- Stamford
After a short classroom session students spend up to an hour in a pool learning basic scuba skills from certified instructors
Angler Fishing Fleet
- Port Washington
39-passenger fishing vessel furnished with sonar, wraparound deck, equipment, and bait
New York Sailing School
- New Rochelle
Learn the fundamentals of sailing, from trimming the sails to operating the boat, while skimming across the Long Island Sound in a Sonar 23
North Star II Fishing & Charter Boat
- Gilgo-Oak Beach-Captree
Experienced crew leads up to 40 passengers in the hunt for fluke, flounder, and eel bass during half-day and night seaborne sojourns
Hamptons Adventure Watersports
- Southampton
CPR-certified instructors beckon students into Hampton's waters to learn to balance, paddle, and explore atop standup paddleboards
Long Island Stand-Up Paddle Boarding Co.
- East Patchogue
Instructors teach students basic paddleboarding techniques for propelling, maneuvering, and how to read tide and wind conditions
Cosmic Kites
- Hempstead
Groups of up to four students learn essentials of kiteboarding; lessons are taught on land and in water and cover all safety aspects.
JK Kayak
- Huntington
Certified instructors lead paddlers through Long Island waterways and secluded harbors
Port Sailing School
- Port Washington
Sails billow and marine air nourishes lungs as students learn to helm Sonar 23 keelboats in semiprivate lessons or two-week youth camps
Kostal Paddle
- Multiple Locations
Certified lifeguard and safety instructor teaches balance, steering, and turning before taking students for a tour of the coastline
Cedarbrook Country Club
- Old Brookville
PGA Class A pro Tom Herzog refines swings or short-game techniques in private 30-minute lessons
Fire Island Kite & SUP
- Great River
Experienced instructors teach lessons and guide tours of sites such as Atlantique and Kismet, or rent out paddleboards for self-guided journ
Queens Archery
- Flushing
Hands-on archery lesson introduces beginners to fundamentals & skill practice using rental equipment, adding $10 toward next visit
Shore Thing Rentals
- Glen Cove
Pedal through Glen Cove's nature preserves on a bicycle or tricycle, or glide through Long Island Sound's waters on a kayak or paddleboard
Stable Mates Equestrian Center
Instruction focuses on proper techniques at a walk-trot gait or teaches polo skills; summer camps are filled with horse-related activities
Turtle Cove Golf Center
- City Island
Windmills thwart hole-in-ones during mini golf, and guests take aim at better swings and flop shots on the driving range
Greenlawn Equestrian Center
- Greenlawn
Led by walkers, ponies trot down a trail that runs around the equestrian center and through the nearby woods; rides last around 10 minutes
Recommended Outdoor Activities by Groupon Customers
At Connecticut Cycle Center, indoor spinning classes or triathlon training with coach Kelli Montgomery beckon students to wheel in their own bikes and affix them to cycling apparatuses. Both classes and training sessions emulate outdoor adventures thanks to ErgVideo and CompuTrainer systems, which mimic famous routes on TV screens. Virtual Tour de France inclines or Spanish plains challenge cyclists to push their endurance to the brink as they mingle with peers. Classes, like the art of hanging out in an operating laundry machine, range from beginner base spins to high-power interval training. Feedback after each session charts your ascent to fitness. High-quality Apex bikes are available for rental and can be taken to nearby roads for an alfresco adventure.
A crack rings out from the jousting arena as armored knights clash in the pursuit of honor, while sword-swallowers thrill crowds with their death-defying art, jesters spin windy jokes, and townspeople in 15th-century garb roam the grounds tearing into turkey legs with their teeth. The Connecticut Renaissance Faire hosts these medieval-theme blowouts every year, including the Robin Hood Spring Festival and King Arthur’s Fall Harvest Faire. Under the themed umbrella of each gathering, actors caper about a constructed medieval village, engaging in Old English–flavored conversation and clapping games with fair-goers. In a tented marketplace, vendors sell beaded crafts, art, and tyrannical-king repellent alongside stands serving mead, beer, and other satisfying sundries. Although the shows and events vary at each fair, past spectacles have included archery displays, pub sing-alongs, and costume parades.
Hand-painted murals of surreal city skylines, rolling fields, and sunrise-speckled ocean views surround customers inside The Hub, a full service bicycle shop and service center. In the midst of the modern artwork, a dedicated crew works to equip riders with gear for pedaling past similar scenes in the natural world, relying on expertise they’ve gleaned from working in development and design with K2 bikes to maintain and repair rides. The knowledgeable staff guides cyclists through expansive show-room floors filled with parts, helmets, and bicycles of various styles including BMX, road bikes, mountain bikes, and beach cruisers from brands such as BMC, Kona, Bianchi, and K2. Bike riders themselves, the staffers work to educate each customer who walks through the door, championing the environmentally friendly form of transportation beloved by small, lazy dogs in baskets everywhere.
During your tasting for two ($5 value per person), you'll sample five different red and whites from Osprey's superb selection. The award-winning grapen goodness is culled from lively vinifera vines creeping across the 90-acre grape growery. Spend time sipping in Osprey's comfortable tasting room and scouring the sky above the sun-bathed rows of green for soaring ospreys, who guard grapes from liquor-loving kobolds. The take-home bottle of 2006 reserve chardonnay ($15 value), a full-bodied sip that's ripe with aromas of tropical fruit, toasted oak, and vanilla, has a well-balanced acidity that pairs well with seafood and sea-smoothed stones. Check Osprey's Dominion's schedule of events to see when there's live music.
Jenks Productions has been handling the nuts and bolts of consumer trade shows for 33 years. Partnering with local and national businesses, Jenks specializes in home, bridal, and pet shows, which fill sprawling spaces with vendors eager to share their wares and visitors looking for inspiration. The services that Jenks Productions provides are extensive, as the team can do everything from onsite event management and budget planning to marketing efforts such as developing newsletters, logos, and jingles that rhyme the words “impending nuptials.”
A full quarter mile of outdoor track snakes across the grass, sending racers on an adrenaline-fueled grudge match of hairpin turns, pedal-pushing straightaways, and close finishes. A speedy fleet of go-karts sends drivers flying down the track in vehicles such as the swift 9-horsepower Interceptor, or the two-seater Tornado, which allows children to ride alongside their parents to learn proper three-point turn technique. An on-track scoreboard displays racers’ lap times with accuracy up to a 1,000th of a second, and printed results enshrine automotive achievements and bragging rights for display. Inside, a beeping, blinking arcade pits gamers head-to-head in pro-racing simulators, bouts of Guitar Hero, or rousing tournaments of air hockey.
