The Weekend Guide: June 22nd – June 24th | Portland Old Port

The Weekend Guide for June 22nd – June 24th

We’ve got lots of boats, lots of wine, dogs, food, and drinks to enjoy in the Old Port this weekend, so, I guess you could say Summer is getting pretty serious.


One of Portland’s best summer traditions, Tall Ships Portland Schoonerfest & Regatta is here! Enjoy the sights of the tall ships, schooner races and parades under sail in the Portland Harbor all weekend long, and maybe even catch a ride on a racing schooner!

When dogs and Sea Dogs come together, it’s a good night. Bring your pup out to the ballgame for Bark in the Park, a special dog-friendly Sea Dogs game at Hadlock Field to benefit the Planet Dog Foundation!

Lettuce enjoy the music of the band, Lettuce as they kick off their 2nd Annual Lettuce Eat to benefit Full Plates Full Potential, whose works connect hungry Maine kids with the food they need to thrive. VIP ticket includes multiple courses of small plates provided by the talented culinary team at Duckfat, killer music, and a poster signed by Lettuce.

Would it really be a summer Friday in the Old Port without a stop at The Porthole for live music and drinks on Portland’s largest waterfront deck? The answer is no, so catch Sugarbox there from 7-11 pm!


Let’s make one of our favorite places a little bit more beautiful, shall we? Clean Up the Cove! With the Maine Public Health Association from 1:30-3:30 pm, all are welcome to partake and trash bags & gloves will be provided for the sake of better enjoyment of the beautiful Back Cove.

Allagash Brewing Company is hosting their annual Street Fair, filled with music, food, beer, performances, and fun events for all ages, starting at 1 pm!

Explore the history and wide-ranging style of Napa wines as you taste your way through 6 different wines (also the option for a four-course dinner of mouth-watering cuisine) in honor of Portland Wine Week at Bolster, Snow & Co. starting at 2 pm.

Grab your grass skirts and your best tropical attire for a Hawaiian Luau Pub Crawl! Hula on down through 10 different Old Port bars for incredible drink specials and a chance to win CountryFest tickets and $2,000 in door prizes!


Round out your weekend with a little meditative exercise with Yoga in the Outfield, hosted by Maine YogaFest and the Portland Sea Dogs to benefit Maine Children’s Cancer Program. Bring your own mat for this all-skill-levels event, starting at 10 am and followed by a Sea Dogs game!

One more cruise to end your weekend, why not? Climb aboard the Casablanca at 2 pm for a cruise featuring dinner and a party with the music stylings of Something Stupid.

The Closing Gala of Portland Wine Week will be a Celebration of Wine, Food, and High-Flying Fun and the perfect clincher for your weekend at O’Maine Studios that will also benefit the Preble Street Teen Center and showcase five generous courses from five of Portland, Maine’s finest and most acclaimed chefs, starting at 4 pm.