A weekend in Portland can include a mix of sightseeing, food, and outdoor activities. Some popular things to do in Portland Maine include exploring the Old Port, visiting Portland Head Light, walking around the Eastern Promenade, and discovering local restaurants and breweries. You can also spend time browsing independent shops or taking a harbor cruise if the weather is suitable. Since many attractions are relatively close to one another, creating a flexible itinerary can help you enjoy the city without trying to fit too much into one weekend.