Official Tourism Site for the Greater Portland Region of Maine


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Official Tourism Site of Greater Portland Maine
Visit Portland Things To Do
207-772-5800 |

5 Can’t Miss Fall Festivals

Greater Portland’s exciting line-up of Fall events

Why should summer get to have all the fun? Hayrides, harvesting apples, and carvings pumpkins–all your favorite Fall activities are back. And no one does Fall better than Greater Portland. Come join in on the sweater weather and vibrant Fall colors. Our popular annual festivals are back and better than ever along with some new additions to brighten the line-up of events. See you there!

Maine Brew Fest

September 13-15, Newry

Tis’ the saison! Maine Brew Fest is back for their Fall session and this time it is a full weekend packed with beer-themed events at the scenic Sunday River Resort + Conference Center. The weekend begins on Friday night with a Chondola ride to the mountainside Peak Lodge for a delicious seasonally-themed dinner with live music and you guessed it, plenty of beer. The rest of the weekend is filled with food trucks, beer tastings, and their Maine OysterBrew event pairing local oysters with craft beer. There is plenty on tap outside beer activities as well like disc golf, ziplines, and scenic Fall lift rides.

Cumberland Country Fair

September 22-28, Cumberland

Get in touch with Maine’s agricultural roots at the Cumberland Fair. The epitome of tradition, this historic event started in the 1800s and today it has everything you would expect from a local fair. There are carnival rides, a petting zoo, and of course lots of indulgent fair foods—friend dough, candy apples, cotton candy. There are also unique experiences you don’t find everywhere like the annual pumpkin weigh-off and pig races. New this year the fair will be bringing in the Rawhide Rodeo for some family-friendly excitement to take place on Wednesday and Thursday evening, September 25-26.

Portland Harvest Festival

September 29, Portland

Deering Oaks is a 55-acre public park in Downtown Portland with tennis courts, a playground, and a pond. Every year, Portland Harvest Festival is held there to celebrate Portland and the coming Fall harvest. Surrounded by the lush grounds of the park you will find food trucks, live music, and plenty of activities. Kids will enjoy the bouncy houses, face painting, and free horse and wagon rides throughout the park.

Freeport Fall Festival

October 4-6, Freeport

The Freeport Festival is a celebration of art, music, and food in the heart of Freeport. The charming seaside town of Freeport, Maine is just twenty minutes outside of Portland and is surrounded by shopping opportunities like outlets, boutiques, and of course the 24-hour L.L.Bean Flagship store. Over 100 artists’ exhibit works ranging from photography, oil, watercolor, mixed media, fine craft, and jewelry so you can find the perfect Maine made souvenir to take home with you.

Harvest on the Harbor

October 17-20, Portland

Portland’s premier food + spirits festival is back with a diverse (and delicious) line-up of events this October. This highly anticipated yearly event is kicking-off with a Chef + Farmer Harvest Dinner; a celebration of local chefs and farmers collaborating to deliver a beautiful, three-course dinner with local wine/beer pairings along the way. With fresh ideas to invigorate the annual event–and their new location at Brick South at Thompson’s Point–it is sure to be an unforgettable year for Harvest on the Harbor.

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