Candlewood Isle and the surrounding area is more rural than southern Fairfield and Westchester counties and offers many year round activities year. 

Summer:

• Children's Camp Program on the Isle
• Cocktails on the beach on weekends
• Annual July 4th Family Fun and Fireworks
• Swimming at the clubhouse beach
• Kayaking/Canoeing Racks are available at the clubhouse to store your kayak. Contact the harbor master to get on the waitlist.
• Boating If you have a boat and would like to get on the waitlist for an Isle slip or mooring, contact the harbormaster.
• Fishing in the lake or Housatonic
• Water skiing/Tubing
• Golf - Richter Park, Candlewood Valley Club
• Horseback Riding
• Farm stands (all over, including Gus's on the Isle)

Fall:

• Apple picking 
• Pumpkin Picking
• Hiking nearby in Pootatuck State Forest at Squantz Pond  or the Appalachian Trail
• Foliage
• Kayaking/Canoeing 
• Annual Isle Chili Cookoff
  

Winter:

• Skating on the frozen lake
• Snow shoeing on the frozen lake
• Ice fishing
• Skiing (Thunder Ridge 20 min, Mohawk 45 min, Catamount 1 hour, Butternut 1 hour, Jiminy Peak 2 hr)

Residents can also enjoy many attractions in the surrounding area year round:

• New York City (1.5 hour to midtown)
• Stepping Stones Children's Museum (45 minutes)
• Maritime Center (45 minutes)
• Mohegan Sun (1.5 hour)
• Foxwoods (1.5 hour)
• Mystic Seaport (1.5 hour)