A Great Guide to an Epic Day in Portland Maine

“We’re going to spend the day in Portland Maine.” – an often heard statement of our guests at the Wolf Cove Inn, a bed and breakfast in Maine. Well known as one of the foodiest small cities in the US, folks love enjoying a great breakfast at the Inn then heading into Portland for the day of adventure, site-seeing and touring. Here’s your guide to some favorite things to do in Portland, Maine for a great day in the big city.


Lobster traps on a dock and fishing boats in Portland Maine

Your Day In Portland Maine

Homey and sophisticated at the same time, plaid flannel meets grey flannel in a funky embrace in Portland. Home to a working port providing adventure on the high seas, Portland offers a wide variety of enjoyable activities satisfying most any traveler’s urge. From culinary to historic, explore Portland’s seafaring roots with that authentic Maine vibe.

A Brief History Of Portland

Native Americans called the Casco Bay peninsula “Machigonne”, meaning great neck. On a grant, Captain Christopher Levitt founded the original 6000 acre settlement in 1623. The first permanent settlement in 1632 saw the establishment of a fishing and trading village named “Casco.” Upon take over by the Massachusetts Bay Trading Company in 1658, “Falmouth” replaced Casco as the settlement name. After the Revolutionary War, the town split. The northern part retained the Falmouth name. The southern part took on the name Portland, after the English Isle of Portland. In 1820, Maine became a state with Portland as the capitol.

Though the capitol moved to Augusta in 1832, Portland remains the largest city in Maine. Over 67,000 Mainers call Portland home. Furthermore, today more than 1/3 of Maine’s population reside in the Greater Portland Area.

Congress St Day In Portland Maine

Touring In And Around Portland

Explore Portland by two legs, bike or railroad! Visit lighthouses, Casco Bay islands, Victorian era homes and more.

Walking Tours

Greater Portland Landmarks recommends a number of self guided walking tours of Portland. Tours including:

  • Congress Street Historic District Tour tracing the development of Portland architecture,
  • Old Port Historic District Tour explores Portland’s maritime history and Victorian architecture along with the district shopping scene,
  • Western Promenade Tour features homes with 18th and 19th century architecture,
  • Stained Glass and Steeples Tour covers 15 houses of worship,
  • Munjoy Hill Tour that includes the historic Portland Observatory Museum.

Biking Tours

Summer Feet Cycling offers a wide range of biking tours:

  • A “Five Lighthouse” Bike Tour, including the famous Portland Head Light,
  • An “Explore Casco Bay” Ferry and Bike Tour that includes ferry rides in addition to bike touring of the islands of Casco Bay,
  • A “Bike and Brews” Tour hits up the Portland local craft brew scene,
  • An “Around The Peninsula” Tour covers the history and architecture of Portland,
  • And more …,
  • Before your tour begins, start by picking up your bike at The ENCYCLEPEDIA bike shop on Commercial Street.

Railway Tours

Maine Narrow Gauge Railroad Co. & Museum offers museum tours and then an historic train ride along the Portland and the Casco Bay waterfronts.

Lobstering During A Day In Portland Maine

Portland Adventures On The High Seas

Get out on the high seas and explore the history and roots of Portland and Casco Bay.

  • Want to catch your own Maine lobster? LuckyCatch Cruises will take you on an authentic lobstering expedition,
  • Odyssey Whale Watch offers, you guessed it, whale watching cruises. Sightings may include Finbacks, Humpbacks, Minkes, Dolphins and sea birds. In addition, each trip includes narrated tours of Casco Bay’s lighthouses, forts and islands,
  • The RitaB offers Deep Sea Fishing trips as well as à la carte trips into Casco Bay,
  • Ever wanted an authentic windjammer adventure? Portland Schooner Co. sails two vessels, one built in 1912 and the other in 1924. Explore the waters of Portland Harbor and Casco Bay on these multi-masted pieces of history,
  • Want a little exercise while exploring the Casco Bay islands? Portland Paddle offers sea kayak & paddleboard tours, rentals and lessons.

Visit Victoria Mansion On Your Day Trip In Portland Maine

Portland Historical and Educational Sites

  • Victoria Mansion. Also known as the Morse-Libby house. Spectacular architecture, stunning interiors and exquisite original furnishings. Designated a National Historic Landmark, Ruggles and Olive Morse built their summer home between 1858 and 1860. 109 Danforth Street, Portland Maine
  • The Museum at Portland Head Light. The oldest lighthouse in Maine, Portland Head Light guides maritime traffic through the entrance to Portland Harbor going on over 200 years. 1000 Shore Road, Cape Elizabeth Maine. For more details on visiting, check out my article on A Scenic Day Trip to Portland Head Lighthouse.
  • Colonial Tate House. A National Historic Landmark built in 1755. Portland’s only colonial home open to the public. 1267 Westbrook Street, Portland, Maine
  • Henry Wadsworth Longfellow House & Garden. The oldest brick structure on Portland’s peninsula.  The childhood home of the namesake poet built in 1785 by the poet’s grandfather. 489 Congress Street, Portland Maine
  • Portland Museum of Art houses an extensive collection and nationally renowned exhibitions. Seven Congress Street, Portland, Maine
Dining In Portland Maine

Dine In America’s Foodiest Small City

You Must Eat In This Foodiest Of Cities

You can’t spend a day in Portland Maine without eating something, now can you? Bon Appetite named Portland “2018 Restaurant City of the Year.” And with good reason. Some of the Wolf Cove Inn guest’s favorites include:

  • Duckfat – Our daughter raves about this place. Us – we’ve not been able to get in due to popularity. Sandwiches, salads and OMG fries. How many restaurant chefs can claim a 3-time Food Network “Chopped” championship? 43 Middle Street, Portland, Maine – Lunch and dinner year round, Friday through Monday.
  • Eventide Oyster Company – A great selection of oysters and local seafood with a funky atmosphere. 86 Middle Street, Portland, Maine – Lunch and dinner year round.
  • Scales Restaurant – Located right on a working pier. Premier dining in the Old Port area – a favorite of Sue & Roy. 68 Commercial St, Portland Maine – Dinner year round.
  • DiMillos’s On The Water – Literally on the water. Specializing in local seafood and pasta dishes. 25 Long Wharf, Portland, Maine – Lunch and dinner year round, except Sunday.
  • Portland Lobster Company – As fresh as the seafood gets! Named a top five restaurant in Portland by Epicurious and a perennial “best of Portland” winner. 180 Commercial Street, Portland Maine – Lunch and dinner May-Oct.
  • Green Elephant – A Vegetarian Bistro with Asian inspiration. We’ve had many guests offer glowing praise about the Green Elephant. 608 Congress Street, Portland Maine – lunch Thursday through Saturday, dinner Tuesday through Sunday year round.

Front Entrance To Wolf Cove Inn

Your Stay At The Wolf Cove Inn

So, we’ve told you a lot about spending a day in Portland Maine. Now, about that stay at the Wolf Cove Inn.

Your Maine B&B sits right on the shores of Tripp Lake in Poland Maine. With over 550 feet of private lakefront, we offer the perfect, peaceful location for your romantic getaway in Maine. Start each day with a wonderful, three-course Maine comfort breakfast before hitting the road. Then go have fun in Portland!

Upon returning, enjoy fresh made pizza from our Tripp Lake Pizzeria. Then venture out to the fire pit (grab the gourmet style 1927 S’mores Kits from our gift shop on your way) and enjoy the spectacular sunsets gracing us most evenings.

Next day, get out and explore Tripp Lake with your complimentary kayaks and canoes. Or choose from the wealth of other local activities by browsing all my blog posts about things to do in the area. Topics cover all seasons – winter, spring, summer, fall and mud!


Fire Pit At Sunset At Wolf Cove Inn


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