FALL IN PORTLAND
We are approaching the time of year where crisp air begins to settle in and the foliage paints the coast of Maine in hues of red, orange, and gold. Whether you are a leaf-peeper, foodie, or just seeking to soak up the New England fall spirit, Fore Points Marina is your perfect starting point. Dive into Portland’s autumn season with our guide to foliage, eateries, attractions, and more.
Start the day with a fresh cup of coffee from Bard. Visit the coffee cart right at Fore Points, or head to their cafe on Middle Street for the full menu including a pumpkin spice latte (because ‘tis the season!). Bite into a delicious apple cinnamon donut from The Holy Donut before lacing up your Bean Boots for a day of autumn adventure.
Step off your boat and take a stroll along the Eastern Promenade just outside of Fore Points Marina. Its sweeping views of the bay will take your breath away, and there are a number of picnic areas for you to sit and enjoy an afternoon in the park. Don’t feel like walking? Take a ride on the Maine Narrow Gauge Railroad and take in the scenic views from aboard a train. Check out their “Pumpkin Train” on October 21 & 22!
Fort Sumner Park is another great spot to view the autumn foliage, its position atop a hill creates for a great view of the water and downtown Portland. This autumn, Health Resonates is hosting a number of pop-up classes in the park, so be on the lookout for yoga and other opportunities to get moving outdoors.
For a birds-eye view of the changing colors, climb to the top of the Portland Observatory. The tower offers panoramic views of Portland and will be perfect for soaking in views of the foliage along the waterfront. The tower was built in 1807 to be a signaling station for mariners and merchants, and measures 86 feet high.
Portland Headlight is located in Cape Elizabeth and is the oldest lighthouse in the state of Maine, as well as one of the most photographed lighthouses in America. While it is beautiful any time of year, when surrounded by the golden hues of fall, it is sure to amaze.
The islands of Casco Bay boast natural beauty in any season, but especially when sporting their fall foliage colors. Take a ferry to Chebeague Island and have lunch at the Chebeague Island Inn Restaurant. You can even play nine holes of golf at the Great Chebeague Golf Club where you are able to see the ocean from every hole.
Head into town and explore the Old Port – the cobblestone streets and historic architecture combined with falling leaves will feel like a scene out of a movie. Stop into the boutique shops and pick out souvenirs, anything from candles to clothing to plants and so much more.
Speaking of shopping, prepare for the cool weather of a New England autumn by paying a visit to the L.L. Bean Flagship store in Freeport. Just a 20-minute drive from Fore Points, stock up on your flannels, boots, beanies, and more. Take a photo with their iconic “Bean Boot” outside, and grab some accessories for your home and even your furry friends! L.L. Bean is a quintessential New England brand that began right here in Maine, and has been known for their quality outdoor gear for over a century.
Portland’s culinary scene will offer plenty of comfort food to enjoy during your visit. Duckfat is located on Middle Street and is known for its Belgian frites. Enjoy a warm heaping of frites or poutine paired with one of their many local brews. Or stay close to home and dine at Twelve, just steps away from Fore Points. Bite into a warm lobster roll because, after all, you are in Maine!
And what is fall without a festival! Harvest on the Harbor takes place in Portland from October 24th to October 26th and will include the Lobster Chef of the Year Competition, Maine OysterFest, and more. The Freeport Fall Festival is October 4th through 6th in Freeport, Maine, and will be fun for the entire family. Look forward to live music, arts & crafts, and more. And in true fair fashion, the 152nd Cumberland Fair will be held in Cumberland, Maine. Here enjoy parades, fireworks, rides, demolition derbies, livestock events, live music, plenty of food, and so much more! Take in all the fun when the fair returns on September 22nd through the 28th.