Portland and the Greater Portland area have events scheduled all year long. For the most up-to-date listings, head over to and check out their Events Calendar. Here are some of our favorite annual events in and around Portland.


  • Old Port Festival – Portland, Maine – Portland’s annual kick-off to summer!
  • Pride Portland! – Portland, Maine – 10 days & nights of LGBT pride celebrations, events, concerts & parades!
  • Greek Heritage Festival – Portland, Maine – A celebration of Greek food, crafts, music, dancing, and history which brings in over 10,000 visitors during the three-day festival!
  • Bowdoin International Music Festival – Brunswick, Maine – Renowned artists, performers, and instructors performing all month long on the beautiful campus of Bowdoin College.
  • Stars and Stripes Spectacular – Portland, Maine – Portland’s 4th of July fireworks display and festival with the Portland Symphony Orchestra!
  • Old Port Half Marathon – Portland, Maine – Half marathon & 5K through the Old Port & The West with over 3,000 runners annually.
  • Yarmouth Clam Festival – Yarmouth, Maine – Seafood in abundance! Always the third Friday in July.
  • Maine Lobster Festival – Rockland, Maine – Five days of fun in Rockland, Maine! Feast on all the lobster you can eat!
  • Beach to Beacon – Cape Elizabeth, Maine – 10K road race from Crescent Beach State Park to Portland Headlight.
  • Portland Chamber Music Festival – Portland, Maine – The most popular chamber music festival in New England!
  • Maine Highland Games – Topsham, Maine – The largest Scottish Games Day in New England!


  • Fryeburg Fair – Fryeburg, Maine – With over 3,000 animals, this is Maine’s largest agricultural fair!
  • Maine Marathon – Portland, Maine – Marathon, Half Marathon, and Marathon Relay event offers wonderful views of the Portland skyline, Back Bay, Casco Bay, and peak fall foliage. USATF certified and a qualifier for the Boston Marathon.
  • North American Wife Carrying Championship – Newry, Maine – Fun for competitors and spectators alike, teams from across North America compete for fame, fortune, and the opportunity to compete in Finland at the World Championships!
  • Freeport Fall Festival – Freeport, Maine – Art, music & fun in the heart of the Coast!
  • Camp Sunshine / L.L. Bean Pumpkin Festival  – Freeport, Maine – The streets of Freeport are turned into a sea of pumpkins!
  • Harvest on the Harbor  – Portland, Maine – Portland’s largest food & beverage festivals celebrating local foods and local talent.


  • Portland Beer Week – Portland, Maine – Beer enthusiasts unite!
  • Annual Christmas Prelude – Kennebunkport, Maine – Kennebunkport’s kick-off celebration of the Christmas season!
  • Sparkle Weekend – Freeport, Maine – Freeport, Maine welcomes visitors from around the world to celebrate all things magical about the holiday season!
  • Magic of Christmas – Portland, Maine – Celebrate the stories and traditions of the season with the Portland Symphony Orchestra and special guests!
  • Maine Lakes Region Winter Carnival – Bridgton, Maine – A winter carnival with mushing, skijoring, ice skating, snowmobile rides, carriage rides, snowshoeing, ice fishing, and food!


  • Maine Restaurant Week – State-wide – When Maine’s lodging and restaurant professionals roll out the red carpet!
  • Maine Maple Sunday – State-wide – Join Maine’s Maple Producers as they open up their Sugar House Doors!