May-September guide book
Sightseeing
Portland Museum of Art
7 Congress SqSmall but mighty art museum.
Maine Historical Society
489 Congress StBeautiful park with great photo ops of the Portland Headlight lighthouse, a small beach and scenic trails along the ocean. At this park, you will experience the classic Maine coastline. Great for a picnic!
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Fort Williams Park
1000 Shore RdBeautiful park with great photo ops of the Portland Headlight lighthouse, a small beach and scenic trails along the ocean. At this park, you will experience the classic Maine coastline. Great for a picnic!
Great views of Hussey Sound, a beach (with bathrooms) and on the Portland Trails system—one mile walk into the Old Port from here.
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Eastern Promenade Trail
Eastern PromenadeGreat views of Hussey Sound, a beach (with bathrooms) and on the Portland Trails system—one mile walk into the Old Port from here.
On the Greenbelt Pathway in South Portland, this park is adored by locals who often picnic and fly kites there. Beautiful views of Portland and a lovely walk along the water to the campus of Southern Maine Technical College where there is a historical museum.
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Bug Light Park
On the Greenbelt Pathway in South Portland, this park is adored by locals who often picnic and fly kites there. Beautiful views of Portland and a lovely walk along the water to the campus of Southern Maine Technical College where there is a historical museum.
This lounge is at the top of the Westin Hotel and offers panoramic views of Portland’s Arts District.
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Top of the East
157 High StThis lounge is at the top of the Westin Hotel and offers panoramic views of Portland’s Arts District.
The Farmers Market is held here every Saturday morning. The park is great for relaxing, picnicking or a tennis or volleyball match!
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Deering Oaks Park
The Farmers Market is held here every Saturday morning. The park is great for relaxing, picnicking or a tennis or volleyball match!
Head to the terminal to buy day-trip tickets to one of the many islands in Casco Bay. Peak’s Island is a popular destination. Or, just enjoy the sights on the Mailboat Run.
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Casco Bay Lines station
Head to the terminal to buy day-trip tickets to one of the many islands in Casco Bay. Peak’s Island is a popular destination. Or, just enjoy the sights on the Mailboat Run.
Great views of Hussey Sound and Portland. Offers information on Portland’s history.
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Portland Observatory
138 Congress StGreat views of Hussey Sound and Portland. Offers information on Portland’s history.
Do you want to try your hand at lobstering? If you catch a lobster it’s yours to keep and have cooked at Portland Lobster Company! Learn about the industry by heading to sea on a working lobster boat. Make reservations ASAP.
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Lucky Catch Cruises
170 Commercial StDo you want to try your hand at lobstering? If you catch a lobster it’s yours to keep and have cooked at Portland Lobster Company! Learn about the industry by heading to sea on a working lobster boat. Make reservations ASAP.
Victoria Mansion
109 Danforth StLearn about early Maine history and the ship mast industry. Very informative museum.
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Tate House Museum
1267 Westbrook StLearn about early Maine history and the ship mast industry. Very informative museum.
Relaxing/exercising
Wanting a beach day to hang out in the sun? This is one of the best swimming beaches.
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Scarborough Beach
Black Point RdWanting a beach day to hang out in the sun? This is one of the best swimming beaches.
Rent kayaks or walk the trail through the marsh. Learn about the local wildlife.
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Scarborough Marsh Audubon Center
92 Pine Point RdRent kayaks or walk the trail through the marsh. Learn about the local wildlife.
I don’t recommend dining here, but highly recommend a drink on one of the decks or in the lounge. Parking is free if you get your ticket stamped at the purser’s desk.
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DiMillo's On The Water
25 Long WharfI don’t recommend dining here, but highly recommend a drink on one of the decks or in the lounge. Parking is free if you get your ticket stamped at the purser’s desk.
Did you know LLBean is open 24 hours/day?! LLBean is a compound of several stores in the heart of Freeport. Freeport is a shopping destination for tourists and locals alike. LL Bean also offers the Outdoor Discovery School where you can book lessons in archery, fly fishing, kayaking, etc.
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L.L. Bean Factory Store
95 Main StDid you know LLBean is open 24 hours/day?! LLBean is a compound of several stores in the heart of Freeport. Freeport is a shopping destination for tourists and locals alike. LL Bean also offers the Outdoor Discovery School where you can book lessons in archery, fly fishing, kayaking, etc.
In Pownal, this hike is a short walk to a beautiful summit overlooking forested land. There are trails allowing you to extend your hike to 6+ miles.
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Bradbury Mountain State Park
528 Hallowell RdIn Pownal, this hike is a short walk to a beautiful summit overlooking forested land. There are trails allowing you to extend your hike to 6+ miles.
Every seat is a good one. Check their website for games and information. The fireworks are spectacular.
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Portland Sea Dogs
271 Park AveEvery seat is a good one. Check their website for games and information. The fireworks are spectacular.
Presumpscot River Preserve
99 Overset RdEasy hiking trails. Lovely, forested land.
Food scene
Southern Maine has many outstanding restaurants of all types. I’ve provided traditional Maine seafood options, only.
In Freeport, this place has traditional lobster dinners and lobster rolls. If you are headed to LLBean, make this your lunch destination.
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Harraseeket Lunch and Lobster Company
36 Main StIn Freeport, this place has traditional lobster dinners and lobster rolls. If you are headed to LLBean, make this your lunch destination.
Right on the ocean! Long lines, but great views and traditional lobster dinners. There is a gift shop.
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The Lobster Shack at Two Lights
225 Two Lights RdRight on the ocean! Long lines, but great views and traditional lobster dinners. There is a gift shop.
This restaurant serves the freshest local (Maine) oysters. Excellent quality.
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Maine Oyster Company
38 Portland StThis restaurant serves the freshest local (Maine) oysters. Excellent quality.
Charming, award winning, high-end seafood restaurant in the Old Port.
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Street & Co
33 Wharf StCharming, award winning, high-end seafood restaurant in the Old Port.