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.
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).
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.
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.
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.
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.