Southern Maine Fall Activities in October

Though we all know and love Maine for its balmy summer days, our state is equally (if not even more so!) notorious for its breathtaking autumn. Comfortable temperatures, peak foliage and an abundance of events to enjoy make this season a favorite for many! If you’re looking for fall fun, you’ve come to the right place – keep reading for the best Southern Maine fall activities that are happening in October!

Freeport Fall Festival at L.L. Bean

Freeport, Maine

During the weekend of September 30 – October 2, enjoy the annual Freeport Fall Festival hosted on the L.L. Bean Flagship campus! This free-to-attend event is one of Southern Maine’s best fall festivals, bringing together dozens of the best artists in New England. With three days of live music and over 200 vendors boasting delicious food, handcrafted goods and art of all kinds, there is something for everyone at this fun outdoor event!

Ride the Sunday River “Chondola”

Bethel, Maine

Though technically this isn’t considered “southern” Maine, riding the “Chondola” (their combination of a chairlift and gondola) at Sunday River Ski Resort is too great to pass up this October! Every weekend during the fall, take a ride up North Peak for sweeping views of the Mahoosuc Mountains and Sunday River Valley. Located just over an hour north of Portland in Bethel, this will give you an incredible opportunity to see fiery foliage without having to drive too far north!

Makers Market at Thompson’s Point

Portland, Maine

Thompson’s Point Maker’s Market is taking place on Sunday, October 23! There is no better way to support your local Maine artisans than at this wonderful event.. Whatever you are looking for, you are sure to find it here! From jewelry and ceramics to home goods and vintage, there is so much to see. It’s also a great opportunity to get your holiday shopping done on the early side!

Bring your wallet, grab a cocktail (there’s a full bar to enjoy as you shop!), seek out a delicious snack from one of the many food vendors, and enjoy perusing the beautiful goods available.

Fall Fest Bites & Beer at Island Dog Brewing

South Portland, ME

Celebrate Oktoberfest the Maine way! To ring in the season, celebrate with German cuisine and delicious brews at the Fall Fest Bites & Beer, taking place at Island Dog Brewing on Saturday, October 15.

Tickets are $21 and include a variety of menu items, plus a beer of your choice! Enjoy German-style soft pretzels accompanied by beer mustard and beer cheese, wurst skewers with bacon apple kraut, and Schweinebraten – delicious pulled pork shoulder. This tasty menu has been created by Chef Bo Byrne and should not be missed!

There is plenty of free parking at the taproom, which is family and dog-friendly! Purchase your tickets online here!

Maine Mariners Home Opener Game

Portland, ME

Feel the electric energy and excitement of the Maine Mariners as they kick off their 2022-2023 season against the Trois-Rivieres Lions! The Cross Insurance Arena is sure to be buzzing on Saturday, October 22, as the Portland-based affiliate of the Boston Bruins takes to the ice for another incredible season. Purchase your tickets in advance here!

Cumberland Crossing by OceanView

Cumberland Crossing by Oceanview is an active senior living community centrally located in the heart of Southern Maine, just minutes from Portland. Spend your hard-earned retirement experiencing all our beautiful state of Maine has to offer! Our 100% refundable deposit and inclusive monthly maintenance fee allows you to spend less time worrying about the burden of homeownership and more time enjoying what you love.

To learn more about our community at Cumberland Crossing, please contact us today!