OctoberLate October to early November, 3 daysTicket neededold-port
Harvest on the Harbor is Portland's flagship food festival, three days late October featuring the Maine Pour distillers night, the Maine Lobster Chef of the Year competition and a final-day OysterFest on the waterfront.
Focus: Maine seafood, oysters, spirits, lobster
Tip: Tickets via harvestontheharbor.com. The OysterFest sells out earliest; opening-night Maine Pour features distillers and seafood producers.
JulyWednesday-Sunday around the first weekend of August, 5 daysTicket neededold-port
Maine Lobster Festival in Rockland, 75 minutes northeast of Portland, runs Wednesday to Sunday around the first weekend of August (29 July to 2 August 2026), with steamer cookers, a parade and live music at Harbor Park.
Focus: Maine lobster, seafood, Maine craft beer
Tip: 75-minute drive from Portland; the Coastal Trolley provides shuttle service. Single-day admission tickets via the operator site.
JulyFirst weekend in July, 1 dayTicket neededlibbytown
Portland Craft Beer Festival at Thompson's Point runs the first weekend of July annually, featuring 60-plus Maine and US craft breweries pouring samples in the outdoor festival grounds.
Focus: Maine and US craft beer
Tip: Tickets via the operator site; food trucks at the venue. Sun shelter limited, dress for the day.
NovemberFirst two weeks of November, 9 dayseast-bayside
207 Beer Week from the Maine Brewers' Guild runs nine days of brewery events, tap takeovers, brewer dinners and special releases across Portland breweries and bars in the first half of November.
Focus: Maine craft beer, brewery events
Tip: Most events drop-in; some special-release tap takeovers require pre-booking via the brewery sites.
JuneFirst Saturday in June, 1 dayold-port
Old Port Festival in early June closes the Old Port to cars across Exchange Street with three live-music stages, food and craft-beer vendors and a long day of family programming on the cobbled streets.
Focus: Street food, Maine beer, summer kickoff
Tip: Free admission. Food and drink purchased at vendor stalls. Best entry point is Exchange Street at Middle.