Welcome to South Portland, Cape Elizabeth & Portland

The largest city in the state, Portland offers visitors some of the state’s richest cultural offerings, along with some of its best shopping and serious opportunities to eat (Bon Appétit magazine named Portland Restaurant City of the Year in 2018). Highlights include the islands in Casco Bay, the Old Port and the Arts District. Across the Casco Bay Bridge are the communities of South Portland and Cape Elizabeth, each with historic lighthouses: Spring Point Ledge Light and Bug Light in South Portland and Portland Head Light in Cape Elizabeth at historic Fort Williams.


1. Portland Sea Dogs

Portland Sea Dogs at Hadlock Field. Photo courtesy of the Portland Sea Dogs

Labor Day weekend is your last chance to join the locals at a Portland Sea Dogs game. The Double A minor league affiliate of the Boston Red Sox has sent many a player up to the big leagues, including Jon Lester and Dustin Pedroia. Hadlock Field at 271 Park Ave. in Portland features a small version of Fenway Park’s famous Green Monster and a lighthouse that rises above the fence whenever a Sea Dogs player hits a homer. Also, good fries, no bad seats, cheap tickets and a decent lobster roll. (207–879–9500;

2. Portland Museum of Art

The Portland Museum of Art’s extensive collection ranges from Andy Warhol and Winslow Homer (tons of Homer) to Louise Nevelson and Claude Monet. Current exhibits include The Expansion of Cubism, 1911–1920. There’s also a show focusing on new acquisitions. Bargain alert if traveling with young people; thanks to the Susie Konkel Pass, everyone age 21 and younger can visit the PMA for free. Visits on Friday nights, 4–8 p.m. are free for everyone. Otherwise, general admission is $18 with separate ticketing for films. The PMA is at 7 Congress Square in Portland. (

3. First Friday Art Walk

Friday Art Walk, on the first Friday evening of the month year-round, is a cultural event that attracts thousands of people to Portland, primarily to the Arts District, for a free self-guided tour of artsy stuff, both indoors and out. First Friday Art Walk is a bit like a monthly citywide reunion (and one of the few times it’s next to impossible to find parking in this usually quite drivable city). For a list of the art galleries, studios, museums and alternative art venues open from 5 to 8 p.m., check

4. Ripple Across Portland

At this second annual, 21-plus adventure race, teams of six will tap into the Social Scavenger app to compete in an epic series of challenges throughout Portland on Saturday, Sept. 28, from 9 a.m. to noon. Challenges range from the easy, like asking strangers their favorite song and then singing it, to harder tricks like say, building a raft with duct tape, then completing a challenge in Casco Bay. The winners earn a lobster bake on Cow Island. The fun starts with a pre-party on Friday night and ends with a celebration on Saturday that includes local food, tasty (adult) beverages and music. Teams fundraise for Rippleffect, a nonprofit that promotes youth development and leadership through adventure, healthy communities and living sustainably. (

5. Bayside Bowl’s Rooftop Fun

Bayside Bowl’s Rooftop. Photo by Taylor Roberge

Portland might not have a lot of skyscrapers, but it does have a fantastic spot to hang out of a roof on a late summer night: Bayside Bowl, where you can eat tacos from a permanently parked food truck, admire sunset over Back Cove, listen to live music, with bands like Johnny Cremains and Big Daddy Kane, or on select nights, watch a movie. The Rooftop Film Series runs through September. Look for Us on Sept. 4, Chocolat on Sept. 25. Admission is free, so grab a taco and a beer and enjoy the movie. (

6. Portland Head Light

Portland Head Light

Commissioned by President George Washington and built in 1791, Portland Head Light is located 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 features lighthouse lenses and a variety of interpretative displays. Also onsite is a seasonal gift shop that sells Maine tourist stuff. The museum and gift shop are open daily, 10 a.m. to 4 p.m., from Memorial Day to Oct. 31. The fort is located at 1000 Shore Road, Cape Elizabeth. Need a lobster roll afterwards? The Bite Into Maine food truck is parked right there. (Museum admission is $2 for adults, $1 for ages 6–18; 207–799–2661;

7. Spring Point Ledge Light

Spring Point Ledge Light

Spring Point Ledge Light in South Portland is the only caisson-style lighthouse in the United States that is accessible by land and one of the few lighthouses in Maine that is regularly open for tours. The lighthouse is staffed by volunteers who open the lighthouse for tours many Saturdays, Sundays and Tuesdays between Memorial Day and Labor Day ($5 per person). It’s a bit of a scramble—definitely not handicapped accessible—requiring sturdy shoes as you traverse a 950-foot-long granite breakwater that juts into the harbor from historic Fort Preble. Due to the steepness of the ladders, children under 51 inches won’t be allowed up into the tower. To visit the lighthouse off Fort Road, don’t be surprised that you drive through the Southern Maine Community College campus. (

8. Portland Greenfest

This free, environmentally-themed festival, now in its sixth year, is Saturday, Sept. 7, from 10 a.m. to 4 p.m. at Portland’s Monument Square. Check out the more than 40 exhibitors, as well as a kids’ pollinator parade at noon, kids’ crafts, a garden produce swap (bring your extras!), demos on composting and food preservation, a smoothie-making bike, a ride-and-drive with a fancy new hybrid and live music all day. (

9. Sunset Wine Sail on Casco Bay

Set sail on a 74-foot sailboat, the Frances, for a cruise around Casco Bay with sommelier Erica Archer. There are multiple cruises on Fridays, Saturdays and Sundays at midday and in the sunset hours throughout Sept. and Oct., focusing on different varietals and regions, including Spanish, Piedmont and Greek wines. Some cruises feature local chefs. Meet at Maine State Pier, 56 Commercial St., Portland. (

10. Casco Bay Lines

Casco Bay Lines

To really get away from it all, there’s nothing like a trip on Casco Bay Lines’ ferries to one of the seven island stops in the bay. If you’ve only got part of a day, take the 17-minute ferry to Peak’s Island, visit the Fifth Maine Museum or the world’s only Umbrella Cover Museum, and take in the view while savoring an ice cream cone at Down Front. For an authentic glimpse of Maine island life, take the nearly five-hour Mailboat Run, stopping at five islands along the way. Or go full-on touristy and take a round-trip narrated tour to Bailey’s Island, which includes a two-hour layover. Pack a picnic or take advantage of docking at Cook’s Lobster & Ale House. The ferry station is at 56 Commercial St., Portland. (