Welcome to South Portland, Cape Elizabeth & Portland

The largest city in the state, Portland offers visitors a wide variety of arts and entertainment, shopping and dining, and historic and seaside attractions. Highlights include the islands in Casco Bay, the Old Port and the Arts District. Across the Casco Bay Bridge, there’s Spring Point Ledge Light Ledge and Bug Light in South Portland and Portland Head Light in Cape Elizabeth. And, if you’re looking for the state’s largest shopping mall, the Maine Mall in South Portland is where you want to be.


1. Harvest on the Harbor

Harvest on the Harbor. Photo courtesy of Harvest on the Harbor

Celebrate Southern Maine’s crave-worthy cuisine and the people who make it all possible at Portland’s annual food and drink festival Oct. 16–21 at locations around the city. Events include the Lobster Chef of the Year Competition, Different Roads (a culinary journey), On the Rocks (Maine’s best happy hour), Hair of the Dog (an epic Bloody Mary battle and pig roast), Oyster Fest and Market on the Harbor. Event tickets are $40 and up and proceeds benefit Full Plates Full Potential, a program working to put an end to childhood hunger in Maine. (

2. Vintage Fire Truck Sightseeing Tours

Hop on this vintage fire engine, which has seats high above the ground for good views, and tour the Portland Peninsula along Casco Bay, with its picturesque lighthouses, old harbors and Civil War–era forts. Live narration is accompanied by high-resolution photographs from the Maine Historical Society on an onboard multimedia system. If it’s particularly chilly or foggy, borrow a fireman’s coat. Finish the tour in the heart of historic Downtown Portland, where you can spend the rest of your day exploring wharves, boutiques and restaurants after getting the lay of the land. Admission is $24 per adult, and the 50-minute tours run through Oct. 28. For more information and reservations:

3. Wabanaki Film ‘Dawnland’

For most of the 20th century, government agents systematically forced Native American children from their homes and placed them with white families. “Dawnland” follows the Truth and Reconciliation Commission to contemporary Wabanaki communities in Maine to witness intimate moments of truth-telling and healing. Portland Museum of Art (7 Congress Square) is screening this film Oct. 5 at 2 and 6 p.m., Oct. 6 at 2 p.m. and Oct. 7 at 2 p.m. The Oct. 7 screening will be followed by a panel discussion. Tickets for this 86-minute film are $8 general admission/$6 for students with ID. (

4. Ghoulwill Ball

The Ghoulwill Ball is a 21+ costumed dance party that calls for imagination, craftiness and a sense of humor. The idea, after all, is to use Goodwill finds to create an alter-ego. The party is Oct. 20, 711 p.m. at The Portland Club, 156 State St., Portland. Compete for cash prizes in the costume competition and boogie the night away with Motor Booty Affair while supporting Goodwill of Northern New England’s Workforce Fund. Tickets are $15 a head…or $15 even if you don’t have a head. Buy them online before the ball sells out. (

5. Maine Humanities Council: ‘Who is we?’

Each fall, the Dorothy Schwartz Forum brings people together to wrestle with a big idea, and this year’s is “Who is we?” Think, talk, wonder, explore and share a meal with an eclectic mix of intellectuals Oct. 20 from 5–9 p.m. at Congregation Bet Ha’am in South Portland. Tickets are available through

6. Portland Head Light

Portland Head Light

Commissioned by President George Washington and built in 1791, Portland Head Light is on a rocky headland in Cape Elizabeth’s Fort Williams Park. This landmark lighthouse is one of the most visited and photographed in the world and includes the Museum at Portland Head Light, which includes lighthouse lenses and a variety of interpretative displays. A seasonal gift shop sells Maine-related items. The museum and gift shop are open daily, 10 a.m. to 4 p.m. through the end of October. Museum admission is $2 for adults, $1 for ages 6–18. The fort is at 1000 Shore Road, Cape Elizabeth. (

7. Bug Light 5K Run and Walk

Bug Light

The Bug Light 5K on Sunday, Oct. 7 is a professionally timed race on a certified 5K course on South Portland’s waterfront. A Kids Fun Run (for children up to 10 years old) will take place at 8:30 a.m., with the 5K starting at 9 a.m. from the public boat ramp area of Bug Light Park. Cash prizes will be awarded for first- and second-place overall male and female finishers and medals for first- and second-place finishers in age categories. Refreshments are provided after the race. Proceeds will benefit the South Portland Historical Society, its museum, and historic preservation in South Portland. For more information and to register, go to

8. Round1 at the Maine Mall

There’s new fun at the Maine Mall in South Portland: Round1 offers bowling, karaoke, arcade games, billiards, darts and ping pong. Open Monday through Saturday from 10 a.m. to 9 p.m. and Sunday 11 a.m. to 6 p.m.

9. Making Strides Against Breast Cancer

Making Strides Against Breast Cancer. Photo by Shawn Patrick Ouellette/Portland Press Herald

If you’ve never walked in a Making Strides Against Breast Cancer event, it’s time! Witnessing an enormous crowd of breast cancer survivors gather together is incredibly moving and powerful—something everyone, especially every woman, should experience. Sign up through the American Cancer Society and start fundraising. The big event in this area is Oct. 14 at Fort Williams Park (1000 Shore Road) in Cape Elizabeth. The opening ceremony is at 10:30 a.m. with the walk immediately following. (

10. Portland Beer Week

Celebrate everything craft beer in this six-day series of events in and around Portland, Nov. 4–10. Close out the week with the inaugural Winter Session at Thompson’s Point on Nov. 10 for the ultimate afternoon of social drinking. (