The 4 Maine Reasons You’d Regret Skipping Portland This Summer

May 23, 2018

Jutting into a bay of nearly 140 lush, uninhabited islands (plus a few inhabited ones), Portland is part wild child, part sophisticate—and all stunner. In fact, between the centuries-old architecture and seriously salty vibe that still dominate the historic center, “the beautiful town that is seated by the sea” is much as Henry Wadsworth Longfellow recalls in his famed hometown shout-out of 1855.

Of course, vintage and modern aren’t mutually exclusive. And so much is happening here that’s specific to 2018, there’s quite literally no time like the present to go. Four cases in point:

1. Just when everyone thought the eating couldn’t get more epic, it has.

With nearly a decade under its ever-loosening belt as “America’s foodiest small town”—a title bestowed by Bon Appétit—Portland keeps upping the edible ante. Now home to more celebrity chefs than you can shake a sustainable seafood skewer at, the city is introducing a new way for you to meet a whole succession of them.

Union Restaurant, Photo Credit; Zack Bowen

As of June 5—and every Tuesday-Saturday thereafter through November—you can take the Maine Food for Thought tour of six local legends: Union, Evo Kitchen + Bar, Solo Italiano, Scales, East Ender and Piccolo. On your own, you’d be hard-pressed to cram such a lineup into even a long weekend, but this three-hour, $72 bacchanalia gets you VIP access to the restaurants, their chefs and special tasting dishes—plus a crash course on the farmers, fishermen and foragers who star behind the scenes.

2. A wine pilgrimage is now in order, too.

Having already established itself as a serious beer bastion (find out why at the Maine Brewers Guild Summer Session Beer Festival on July 28) and cocktail capital (as you’ll discover at the new Blyth & Burrows), Portland is debuting a major wine festival June 18-24. Created by local sommelier and wine educator Erica Archer, the new Portland Wine Week is a series of almost 50 events—some selling out very quickly—that include winemaker dinners, sparkling-wine sails, wine walks, wine-paired performances and tasting seminars.

Photo Courtesy of

Then there are events that run throughout Wine Week: Try your hand (or palate) at the blind tasting contest at MJ’s Wine Bar, and see what the mollusk of the day is at the Shop’s Bivalves & Bubbles pairing.

3. The fun on the high seas is unprecedented.

As you’d guess from its name and peninsular positioning, Portland is inextricably linked to the sea, with centuries of maritime history and plenty of commercial shipping to this day. But if you tend to place boats in the entertainment and leisure category, this summer’s for you. The legendary Atlantic Cup will see its largest ever group of offshore sailors racing and finishing in Portland (where the festivities last from June 4-10), and the new Portland Schoonerfest and Regatta will bring a striking flotilla of tall ships to town June 22-24.

Photo Courtesy of Calendar Islands Sailing Co.

But perhaps the best addition to the scene is a yacht just launched by the Calendar Islands Sailing Co. Dubbed Nicte Ha, she’s offering the first overnight, multiday sailing charters on the state’s southern coast. Totally customizable—with options that include island-hopping, beach-combing, coastal village visits and the occasional elopement—these trips start at $350 per person and include three gourmet meals daily plus drinks. (The latter flow especially freely in cases of elopement.)

4. The newest summer fest will be music to your ears. 

With traditional celebrations ranging from the Old Port Festival (June 10) to the Bach Virtuosi Festival (June 17-24) to the Yarmouth Clam Festival (July 22-24), Portland is the kind of place that has long known how to throw down in summer.

But on June 24, a brand-new blowout is coming to town: the SummerSide Music and Arts Festival, which will bring a stellar lineup of bluesy, folksy rockers to the Urban Farm Fermentory, where—FYI—failure to try the hard Dry Cidah would be a major party foul. The festival will also feature other artists, from visual to culinary. And who knows? You may even find a spoken word artist on the scene who turns out to be Portland’s next Longfellow.


Related Offers Related Offers & More

More Great Deals & Tips