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 for tourists 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. If you need to hit a shopping mall, the Maine Mall in South Portland, home to Maine’s only Apple store, is it.


1. Portland Sea Dogs

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

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. Eastern League games continue through Labor Day weekend.(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. Summer exhibits include In the Vanguard: Haystack Mountain School of Crafts, 1950–1969 about the rural Maine experimental school’s impact on the counterculture, and a new show, 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. Cirque du Soleil: Crystal

The famous acrobatic circus is in town for seven shows (matinees and evenings from Aug. 7–11 at the Cross Insurance Arena in downtown Portland. And this time, the Cirque du Soleil is on ice. The lead character, Crystal, travels through a surreal world that defies the laws of gravity—on skates. ($38 & up;

4. Sunsets on the Point

Thompson’s Point is host to a lot of summer activities, from its summer concert series along the Fore River in Portland (this month’s shows include Guster for two nights) to regular Maker’s Markets. But every Thursday from 4 p.m. through sunset, this free event includes food trucks, beer, wine, cocktails and lawn games. Weather contingent. Dogs allowed. GPS yourself to 11 Thompson’s Point, Portland (right off I-95). Contact for more information. (

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 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 but flag these dates for August. Isle of Dogs on Aug. 7, Spider-Man: Into the Spider Verse on Aug. 14, Free Solo on Aug. 21, and Spike Lee’s Blackkklansman on Aug. 28. Admission is free, so grab a taco and a beer and enjoy the movie. (

6. Maine Food for Thought Food Tour

Maine Food for Thought Food Tour. Photo by Heidi Kirn

Portland is jammed with great restaurants, many serving seriously local foods. In recent years foodie tours have sprung up to showcase the trend. If you’ve only got a few hours and want to get an insider’s look at Maine’s local food movement, you won’t find a better option than this tour, oriented around sustainability and connections to local farm and fisheries. For $79 the signature tour will take you to six stops where you’ll spend three hours learning about Maine food systems while sampling its potatoes, shellfish and among other things, the best pesto ever. Tours in August typically run Tuesday through Friday with a couple of Saturday bookings as well. (207–619–2075;

7. 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 Saturdays and Sundays at midday and in the sunset hours throughout the month, focusing on different varietals and regions, including the Mediterranean, sparkling wines, Italian wines, the Loire Valley and pinot noir. Meet at Maine State Pier, 56 Commercial St., Portland. (

8. 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. (Museum admission is $2 for adults, $1 for ages 6–18; 207–799–2661;

9. 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. It’s 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—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. (

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. (