Wharf Street Portland Maine, things to do two day itinerary
Wharf Street Portland Maine

40 Things to Do in Portland Maine

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Top Things to Do in Portland Maine

Portland Maine is a seaside town with world-class entertainment, an arts district, and an incredible foodie scene. If you are planning a trip to Portland and looking for the best things to do, see, and eat while visiting, you are in the right place.  You will find salty air, rocky coastlines, a working harbor, old captain homes, lighthouses, cobblestone streets, brick buildings galore, lobster shacks, and craft breweries. Browse the list of must-see attractions, off-the-beaten-path experiences, outdoor activities, and museums to create your personal Portland Maine bucket list. Then, plan the itinerary for your Portland trip with these top things to do, see, and eat. Enjoy your time out of the office!

READ 10 Day Road Trip Through Maine, New Hampshire, and Vermont

Custom House Portland Maine things to do itinerary
Custom House

Things to Do in and Around Portland Maine

Wander the Old Port warehouses

Buy fresh oysters at Harbor Fish Market

Shop for souvenirs along Commercial Street in the Old Port

Photograph Longfellow’s Statue in Longfellow Square

Tour the historic Wadsworth-Longfellow House and Garden

Photograph the

Rainbow Row Houses Portland Maine things to do itinerary
Rainbow Row Houses

Enjoy the Friday Night Art Walk in the Arts District

Check out the views from the Portland Observatory

Eat lobster everything

Go for a bike ride along the Eastern Promenade Trail

Give your feet a break and a soak at Soakology Foot Sanctuary & Teahouse

Go for a swim at East End Beach or explore a tide pool

Go lobstering and have your catch prepared at Portland Lobster Company

Explore contemporary art at the Portland Museum of Art

Portland Maine Museum of Art things to do itinerary
Portland Museum of Art

Go on the Casco Bay mailboat run

Check out the historic headstones at the Eastern Cemetery

Check out the Captains Homes

Go for a romantic walk along the coast of the Portland Headlight

Have a romantic picnic on a schooner in Casco Bay

Spend an evening brewery hopping with the Maine Brew Bus

Pick up some cheese and crackers at Cabot Farmers Annex for a romantic sunset picnic

See the stained glass ceiling window at the historic Victoria Mansion

Take the Real Portland Tour of the city and three lighthouses

Kayak around the historic Fort Gorges

Go whale watching

Photograph the Our Lady of Victories statue in Monument Square

Take the five lighthouse bicycle tour

Spring Point Ledge Lighthouse Portland Maine thinngs to do
Spring Point Ledge Lighthouse

Check out the view from the rooftop deck at Bayside Bowl

Learn about Maine’s railroad history at the Maine Narrow Gauge Railroad Company and Museum

Take a selfie with The Maine Lobsterman sculpture on Temple Street

Buy a bag made of sails from Sea Bags

Check out the view from the parking garage on the corner of Pearl and Fore Street

Take a selfie with Big Foot at the International Cryptozoology Museum

Spend a night out on Wharf Avenue

Eat a red skin hot dog from the cart in Tommy’s Park

Watch the sunset from Ocean Point

Catch a Portland Sea Dogs baseball game

Take a romantic full-moon canoe tour through the Scarborough Marsh

Learn about Portland’s Great Fire on the Portland Vintage Fire Truck

Take a sailing lesson in Casco Bay

Check the Visit Portland website for upcoming festivals, special events, and what’s happening during your stay.

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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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Have a great vacation!