An open air market is planned Saturday, July 23, during the ShineOn Oakland Day at Williams Elementary School, 55 Pleasant St. Submitted photo

The annual Oakfest is back with a weekend of family-fun events planned for Friday, Saturday and Sunday, July 22, 23 and 24, in Oakland.

The weekend will start Friday at the Oakfest Downtown Wine & Dine with live music, food trucks, a beer tent, wine and DACH tasting, street dancing, a children’s scavenger hunt, tours of historic Memorial Hall, all starting at 5 p.m. on Main Street.

The activities are sponsored by Oakland American Legion, Buddies Grocery & Oakland Pharmacy, according to a news release from the ShineOnCass Foundation.

On Saturday, ShineOn Oakland Day festivities begin at 10 a.m. at Williams Elementary School, 55 Pleasant St., with a 75-booth, open air market featuring Maine-made artisans and crafters, an extensive variety of food vendors, and dozens of children’s activities like bounce houses, slides, carnival games, rock wall climbing, Mad Science of Maine, Children’s Discovery Mobile Museum, and Oakland Rocks.

To register for a paint party, visit the town of Oakland website. The event also will include the Classic Cruise Car Show, educational booths, and live bands all day.

Sunday starts with a Kids Fun Run at 8 a.m., followed by the fifth annual Oakfest Paddle, Pedal & Pound Triathlon at 8:30 a.m. at the Oakland Boat Landing, 22 Old Belgrade Ave.


This event for all levels of athletes begins with a 2.5-mile kayak or canoe paddle on Messalonskee Lake, transitioning to a 12-mile bike ride along Messalonskee stream. The final leg is a 3.1-mile run through the town, looping through wooded trails and finishing back at the boat landing.

Registration is $50 for individuals, $80 for a two-person team and $120 for a three-person team. The Kids Fun Run is free. Spectators are welcome to cheer on all participants. To register for the Kids Fun Run and Triathlon, visit

The foundation will be collecting school snack donations for local school food pantries as part of the ShineOnCass Snack Project. Those who wish can bring individually-packaged, nonperishable snack donations to help fill a school bus and stock the shelves this fall for students in need. Donations will be accepted all weekend at Oakfest.

To register a booth, secure a food or vendor space, volunteer, or find more information about Oakfest 2022, call Kathy Paradis at 207-465-7358 or visit

Check out other upcoming area events!

filed under: