Windham/Gray Events & Activities

Winter

  • Sebago Lake Rotary Ice Fishing Derby (February 15 & 16, 2025)
    Enjoy the 24th annual ice fishing derby offering a fun-filled weekend with the Polar Dip, Ice Shack Contest, and other family-friendly activities.

Spring

Summer

  • Windham Summerfest (June 21, 2025)
    Celebrate summer with a lively festival featuring a parade, live music, food vendors, and a stunning fireworks display—one of Windham’s biggest community events!
  • Open Farm Day (July 27, 2025)
    Explore local farms in Gray as they open their doors for tours, workshops, and tastings.
  • Music in the Park (July-August)
    Enjoy free outdoor concerts held on Wednesday’s in Dundee Park. Perfect for relaxing summer evenings.
  • Gray Blueberry Festival (August 9, 2025)
    Celebrate Maine’s iconic blueberries with live entertainment, local vendors, and family-friendly activities.
  • Little Sebago Lake Pirate Parade (July 26, 2025)
    Partake in this fun-filled annual tradition where residents and visitors celebrate summer aboard pirate-themed boats. Join the festivities by dressing up and decorating your boat, or cheer on the lively parade of pirates from the shore!
  • Sebago Lake Triathlon (June 29, 2025)
    From the swim on the clean, clear water of Sebago Lake to the challenging bike course on country roads and run on trails across St. Joseph’s College, the Sebago Lake Triathlon promises you safe scenic races, great post race barbecue, professional announcer and music and more!

Fall

  • Cumberland Fair (September 21 – 27, 2025)
    Enjoy this classic fall event featuring agricultural exhibits, livestock shows, carnival rides, live entertainment, and fair food.
  • Halloween Trick or Treat Trail (October)
    Enjoy a safe, family-friendly trick-or-treat event hosted by community organizations and businesses.

Year-Round Highlights

  • Maine Wildlife Park Events
    Experience seasonal events at the Maine Wildlife Park, including wildlife talks, family days, and holiday-themed activities.