4 min read
Passengers aboard the ferry at Diamond Cove on Great Diamond Island in 2024. (Brianna Soukup/Staff Photographer)

It’s easy for summer to get away from us.

After all the chores, obligations and uncooperative weather, there’s a limited number of days to work through that seasonal bucket list. And then, if you’re deterred by traffic, tired or simply uninspired, you might find yourself defaulting to “next week.”

That option, however, is about to go away. Although many Mainers feel that September, when there are fewer tourists, is actually the best time to enjoy the state’s summer activities, people here are affected by the same things that cause visitor numbers to drop, such as school and sports schedules and seasonal businesses shutting down.

If your life is about to get a lot more hectic, here’s a plan to help pack in all forms of Maine summer fun over Labor Day weekend.

FRIDAY: Out on an island and about town

Get things started right by getting on a ferry and off the mainland.

Make a dinner reservation at Crown Jewel (255 Diamond Ave.) or Diamond’s Edge Restaurant (279 Diamond Ave.) on Great Diamond Island if you can, then check the Casco Bay Lines (56 Commercial St., Portland) schedule to figure out the best boat to board. Or, if you prefer less planning, just hop on the ferry to Peaks Island and find a spot on a deck at one of several restaurants.

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Mariagrazia Zanardi serves a gelato at Gorgeous Gelato in Portland in 2025. (Shawn Patrick Ouellette/Staff Photographer) Purchase this image

Once you’re back in town, choose from two gelato shops in the Old Port (Gelato Fiasco, 425 Fore St.; Gorgeous Gelato, 434 Fore St.) then stroll the charming streets or have a nightcap in a parklet outside Hunt & Alpine (75 Market St.) or Blyth & Burrows (26 Exchange St.) and watch the people walking by.

SATURDAY: The capital of Maine summer fun

For a one-stop shop for summer fun, head to Old Orchard Beach for the day.

In a half-mile stretch of the seaside town, you can sunbathe and make sandcastles on the beach, play arcade games at Palace Playland (1 Old Orchard St.) and a round of mini golf at Pirate’s Cove (70 First St.), ride a roller coaster and a carousel, eat Pier fries and Bill’s pizza (12 Old Orchard St.), shop for souvenirs, sip on a rum bucket and dance to live music on the patio at The Brunswick (39 West Grand Ave.).

People swim in the water at Old Orchard Beach in June. (Derek Davis/Staff Photographer) Purchase this image

If you have any energy left, hit up the water park at Funtown Splashtown (774 Portland Road) in neighboring Saco, then head to Scarborough to refuel with fried clams and other seafood from Ken’s Place (207 Pine Point Road), capped with a cone from Dairy Corner (612 Route 1) on your way out of town.

SUNDAY: Living that lake life

After a busy day among the crowds, it’s time to commune with nature.

Start with the 2- to 3-mile hike up and down Douglas Mountain (Douglas Mountain Road, Sebago) and take in lake views from the top.

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Head to Patch’s Variety (965 Chadbourne Road, Standish) to pick up lobster rolls that locals swear by and bring them with you for a picnic lunch on the shores of Sebago Lake.

Tia Char quickly gets the hang of paddleboarding after being launched in the water at Sebago Trails Paddling Co. in 2020. (Brianna Soukup/Staff Photographer)

While you could head right to the state park (11 Park Access Road, Casco) to enjoy some shark-free swimming, you might instead opt to get on the water in a canoe, kayak or paddleboard rented from Sebago Trails Paddling Co. (1311 Roosevelt Trail, Raymond) and launch onto the lake from there.

Check out what’s playing at the two drive-in movie theaters nearby, the Bridgton Twin (383 Portland Road, Bridgton) and Prides Corner (651 Bridgton Road, Westbrook), and let your film tastes guide you.

MONDAY: Tourist town takeover

As the vacationers make their way home for the season, it’s a great time for us to head to tourist destinations.

Wave to the line of traffic on the other side of the road as you make your way to Boothbay Harbor, stopping first at the Coastal Maine Botanical Gardens (132 Botanical Gardens Drive, Boothbay) to take in the flora in its late-summer glory.

Visitors at the Coastal Maine Botanical Gardens in 2019. (Brianna Soukup/Staff Photographer)

Once in the heart of the harbor town, pop into the many quaint shops and choose from several waterfront dining options, including Boothbay Lobster Wharf (97 Atlantic Ave.), a short walk over the footbridge, where you can select which crustacean you’d like to eat.

Plan ahead and book one of several boat or schooner tours, to see puffins, whales or lighthouses.

Schooners sail around Boothbay Harbor as part of Windjammer Days. (Gregory Rec/Staff Photographer)

To actually visit a lighthouse would require quite a drive from here. So, that might be one to save for next weekend, especially because Sept. 12 is Open Lighthouse Day, when many of them will allow you inside.

With the Sea Dogs’ final homestand wrapping up then as well, you might want to extend your summer just a little more.

Leslie Bridgers is a columnist for the Portland Press Herald, writing about Maine culture, customs and the things we notice and wonder about in our everyday lives. Originally from Connecticut, Leslie came...

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