The Best Annual Festivals & Events in the Greater Portland Region

Portland and the Greater Portland area have events scheduled all year long. For the most up-to-date listings, head over to VisitPortland.com and check out their Events Calendar.

Here are some of our favorite annual events in and around Portland.

Summer

  • First Friday Art Walk – Portland, Maine – Portland’s First Friday Art Walk is the state of Maine’s largest free monthly cultural event. Every month, rain, snow, sleet, or shine, the galleries, museums, alternative venues, and the streets of downtown Portland celebrate the creative culture that makes us one of the best small cities in the country.
  • Portland Wine Week – Portland, Maine – Kick off summer with a week-long festival of events featuring wine, local food, art, and fun activities. Presented by Wine Wise, a local wine education and events company, Portland Wine Week is crafted as a boutique experience for wine enthusiasts of all types—from the casual wine lover to the serious oenophile.
  • Pride Portland! – Portland, Maine – 10 days & nights of LGBT pride celebrations, events, concerts & parades!
  • Sailing Ships Festival – Along the Coast of Maine – Month long sailing festival held along the coast of Maine with on-land activities and dockside access.
  • 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!

Fall

  • First Friday Art Walk – Portland, Maine – Portland’s First Friday Art Walk is the state of Maine’s largest free monthly cultural event. Every month, rain, snow, sleet, or shine, the galleries, museums, alternative venues, and the streets of downtown Portland celebrate the creative culture that makes us one of the best small cities in the country.
  • 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.

Winter

  • First Friday Art Walk – Portland, Maine – Portland’s First Friday Art Walk is the state of Maine’s largest free monthly cultural event. Every month, rain, snow, sleet, or shine, the galleries, museums, alternative venues, and the streets of downtown Portland celebrate the creative culture that makes us one of the best small cities in the country.
  • 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!

Spring

  • First Friday Art Walk – Portland, Maine – Portland’s First Friday Art Walk is the state of Maine’s largest free monthly cultural event. Every month, rain, snow, sleet, or shine, the galleries, museums, alternative venues, and the streets of downtown Portland celebrate the creative culture that makes us one of the best small cities in the country.
  • 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!