PORTLAND — Spectate or come aboard schooners in Portland Harbor. Seven traditional schooners parade under sail Friday, and race Saturday and Sunday. Classic schooners included in this year's fleet: 131' Harvey Gamage of Portland; Schooner Adventure of Gloucester, Mass.; Schooner Alert of Bailey Island; and Marine Maritime Museum's Schooner Mary E. Hometown favorites include: Bagheera, Wendameen and Timberwind, an original Portland pilot schooner. Fleet continues on with the Casco Bay Gaffers Race to Bailey Island on June 24. Proceeds benefit Tall Ships Maine's accredited sail training programs.
WESTBROOK — Legendary guitarist Buddy Guy and Kenny Wayne Shepherd Band, fresh off a new album release, join forces at the newly opened Maine Savings Pavilion at Rock Row. Put on by Waterfront Concerts, the show was initially slated for Friday but was moved forward due to a "routing complication." Special guests are Blues artist Samantha Fish and Maine band Memphis Lightning. Doors open at 5 p.m., show starts at 6 p.m. Tickets: Ticketmaster.
PORTLAND — Paint your own lobster buoy at the Children's Museum & Theatre of Maine. Add your own unique design or paint of the classic Maine patterns. $16/buoy (member’s receive 10% discount). 11:30 a.m. to 12:30 p.m.
PORTLAND — Watch The Sellam Circus School acrobats perform on the lawn at Thompson's Point in Portland. Two stages, the Main Stage and CircusKids Stage, will feature juggling, unicycling, acrobatics, diabolo, trapeze and more. Free workshop for kids at 1 p.m. with "The Bearded Man." Food trucks, wine and craft beer available. Admission is free and leashed dogs are welcome.
PORTLAND — Run 13.1 miles around the Portland peninsula and Back Bay, or take part in an all-new 5K race course through the Old Port. 2019 Shipyard Old Port Half Marathon & 5K participants get a free tank, and can celebrate at the finish line block party with Shipyard beer, ice cream, pizza and live music.
*Find an upcoming road race near you
PORTLAND — Wine tasting event at Casco Bay's Fort Gorges, co-hosted by Portland Wine Week and Friends of Fort Gorges. Sip wine at a secret, oceanfront location then take a boat ride to enjoy a tour of the historic Civil War era fort. Rain or shine. Runs 2:15 to 5:15 p.m. $75 covers transportation, wine tasting with Ned Swain of Devenish Wines, charcuterie and a tour of Gorges.
*Portland Wine Week has several other events planned for 2019.