Greater Portland and Casco Bay Attractions
All year long, there's so much to see and do in and around Casco Bay
From museums and theater to hiking and boating to fairs and festivals, Greater Portland is virtually overflowing with fun and exciting options.
If you enjoy drinking in the sites slowly, Portland boasts an extensive system of trails for walking and biking. Stroll the Eastern Promenade and take in the boats dotting the bay. Or, cruise the islands of Casco Bay.
Casco Bay Lines provides ferry travel to Peaks Island, Great Diamond Island, and several other stops. They also offer private cruises and lobster bakes, perfect for a family reunion, wedding or other special event.
Looking for some live action? Check out the NASCAR sanctioned Beechridge Speedway or harness racing track, Scarborough Downs in Scarborough. For an afternoon or evening of professional sports, take in a Portland Sea Dogs baseball game or a Maine Red Claws basketball game.
For arts and culture, check out the Portland Museum of Art. Tour the Wadsworth- Longfellow House, or explore antique railcars at the Maine Narrow Gauge Railroad Museum before taking a ride on a steam locomotive.
For a fun culinary experience, be sure to visit Dimillo’s On the Water or the Top of the East Lounge. Dimillo’s is an actual floating restaurant in Portland Harbor, while Top of the East offers sweeping views atop The Westin Portland Harborview Hotel. Bring your camera for these visits!
Special fairs and festivals occur year-round in Greater Portland. Portland’s Old Port Festival in June features live music, fresh local food, art and crafts for sale, and activities for children. In July, the Yarmouth Clam Festival, a family-oriented tribute to mollusks, stages a carnival, live music, arts and crafts, and plenty of fresh clam-centric snacks! August heralds the Portland Chamber Music Festival, when nationally renowned musicians perform in a series of concerts, including a children’s concert. September is time for the Cumberland County Fair, a family favorite agriculture fair. The fair includes livestock, harness racing, horticultural exhibits, rides, food, live music and more.
Eat, drink and be merry at Harvest on the Harbor in October. The day after Thanksgiving is Portland’s Annual Christmas Tree Lighting in Monument Square, a family friendly event featuring live music. If the tree lighting doesn’t prime you for the holidays, Freeport’s Sparkle Celebration certainly will. Check out the Parade of Lights, take a free horse-drawn carriage rides while you sip hot chocolate, and make some headway on your holiday shopping with a visit to one of Freeport’s many retail stores and outlets.
For a full listing of the area’s many events, fairs and, festivals, visit the official Events page. You can also download the fully-interactive visitor’s guidebook.
No matter the season, there’s always something to do in Maine’s Greater Portland and Casco Bay region.