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How to Spend the Perfect Weekend in Portland Maine
Portland Maine has everything New England is famous for. It is difficult to determine how to best use a long weekend in Portland Maine, there are so many fun things to see, do, and eat. This 4-day itinerary is jam-packed with must-see sites and top attractions, including, Casco Bay, Portland Head Lighthouse, Old Port, Harbor Fish Market, Victoria Mansion, Wadsworth-Longfellow House and Garden, Portland Fire Museum, sample craft beer and eat fresh seafood, and more. Looking for more options? Check these additional things to do in Portland Maine to supplement this itinerary. Have more time? Spend a day exploring the Downeast Highway. It is possible to travel the world with limited PTO, here’s a day-by-day guide to visit Portland in 4 days. Enjoy your time out of the office!
READ 10 Day Road Trip Through Maine, New Hampshire, and Vermont
Day One: Casco Bay
Fly into the Portland International Jetport and take the hotel shuttle to your accommodation in the Old Port. Check into the hotel and drop off your bags. Portland is known as a foodie city with amazing microbreweries. Take a walk down Commercial Street and do some souvenir shopping. Stop at the Harbor Fish Market for fresh oysters and hop the ferry across Casco Bay to Peaks Island. Pass by Bug Lighthouse and Fort Gorges on the way. Spend some time exploring this neighborhood island and check out the only umbrella cover museum in the world. Return to Portland for dinner; enjoy a lobster roll at Highroller or a panini and Belgian fries at Duck Fat. Stop by the speakeasy in the back of Blyth and Burrows for a craft cocktail before calling it a night.
Day Two: Lighthouses and Lobster
Head to Holy Donut for donuts made from Maine potatoes. I can recommend the sea salt chocolate, lemon, cinnamon sugar, toasted coconut, and maple bacon (I may have stopped here a few times). Learn Portland’s history on the Real Portland Tour of the Old Port and visit three nearby lighthouses (Bug Light, Spring Point Ledge Lighthouse, and the Portland Head Lighthouse). Stop in J’s Oyster and enjoy a bowl of lobster stew for lunch. Take a lobster boat cruise after lunch and enjoy the afternoon learning all things lobster. Back at the harbor take your catch to Portland’s Lobster Co and have it steamed for a traditional lobster dinner. Stop by Gritty McDuff’s, Maine’s original brewpub, for a small-batch ale before returning to the hotel.
Day Three: Historic Old Port and Craft Beer
Eat blueberry pancakes at Becky’s Diner for breakfast then walk up the hill and take a selfie with the Rainbow Row Houses. Tour the historic Victoria Mansion and step into 19th-century life. Walk toward Congress Street and check out Longfellow Square and the Old State Theater. Stop in the Portland Fire Museum and learn about the Great Fire of 1873. Go to Top of the East Bar at the Westin Hotel for panoramic views of Portland and Casco Bay. Enjoy a slice of pizza at Otto’s Pizza or walk down to Tommy Park for a red skin hot dog from the cart. Tour the Wadsworth-Longfellow House and Garden and take a selfie with the Maine Lobsterman sculpture. Climb the observatory for harbor views. Take one of the late afternoon Maine Brew Bus tours and learn about Portland Maine’s craft beer scene. Have dinner at Eventide and feast on oysters. Then, spend the evening on Wharf Street and enjoy a cocktail at Central Provisions.
Day Four: Rocky Coastlines
Get up early and take a walk along the Eastern Promenade, past Fort Allen Park, and the Captains Homes. Stop to watch the sunrise. Grab a pastry at Standard Baking Co for breakfast and a few whoopie pies from Two Fat Cats for the flight. Return to the hotel to collect your bags and make your way to the airport via the hotel shuttle.
Be sure to check the Visit Portland website for upcoming festivals, special events, and what’s happening during your stay.
Bookmark and Pin Weekend in Portland Maine
Many thanks to Visit Portland for providing tour opportunities while in Portland Maine. As always, all opinions are my own.
Plan Your Trip to Portland Maine
Portland Maine Travel Guide
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Book Your Accommodation in Portland Maine Now
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Portland Maine Attractions and Day Tours
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Travel Essentials
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Have a great vacation!