Lobster Meets Lighthouse! Take a Weekend Trip to Portland, Maine

Situated on a peninsula in Casco Bay on the Gulf of Maine and the Atlantic Ocean is the charming city of Portland. If you’re searching for a destination that’ll leave you relaxed and and fill you up with succulent seafood, a weekend trip to Portland is the perfect destination. There’s so much to do and see in this city, but a weekend trip is plenty of time to experience Portland if you carefully plan your itinerary.

Once you visit this quaint city, you’ll return home raving about how charming and welcoming it is, not to mention its fascinating history. So, to make sure you won’t leave anything out of your fun-filled weekend, follow our list of what to do in Portland, Maine.

Capture the Portland Head Light

Ever come across a painting or photograph of a tall, white lighthouse with waves crashing against the rocks below? Odds are you were looking at the Portland Head Lighthouse in Cape Elizabeth. It’s one of the most photographed lighthouses in the U.S. and is just about 6 or 7 miles outside Downtown Portland. Head Lighthouse was built in 1791, making it the oldest lighthouse in Maine. Besides seeing the famous lighthouse, you can also visit Fort Williams Park and learn about the history of the fort, walk along the cliffs and rocks, and even fly a kite.

Take a Ferry to Peaks Island

If you want to escape the city for a while, head to Peaks Island. It’s just a 17-minute ferry ride off the coast of Portland and is part of the Casco Bay Islands. There are six islands that make up the Casco Bay Islands, but Peaks Island is closest to the coast of Portland and has many things for visitors to do. You can go shopping, enjoy the beaches, tour museums, and eat at cozy cafés.

Check out Portland’s Art District

The museums and art galleries in and around Portland’s Art District are a must-visit for tourists. Here, you’ll find the Portland Museum of Art, the Children’s Museum and Theatre of Maine, and much more. If you appreciate art, love history, or are traveling with kids, Portland’s Art District is well worth a stroll-through.

Tour the Victoria Mansion

The Victoria Mansion, built from 1858 to 1860, brings the style and charm of the 19th century to life. This site invites tourists to explore its collections from the mid-Victorian period. In this museum, you’ll find the rooms are filled with furniture designed by Gustave Herter, founder of one of the first furniture and interior design firms in the United States. As you walk through the rooms in the mansion, tour guides will teach you about Maine’s history and answer any questions about this National Historic Landmark.

Enjoy the Lobster…

If you love seafood, perhaps while watching live entertainment, then you’ve come to the right city. Portland offers an array of waterfront restaurants serving up fresh seafood with live bands throughout the summer. Popular places for live entertainment and fresh food are Portland Lobster Company located in the Old Port, as well as The High Roller Lobster Co. for one of the best lobster rolls in town. Oh, and if you’re not too fond of seafood — or perhaps are allergic — the restaurants have many other options, like burgers, as well.

…And Clams…

Start your clam-eating tour with a stop at Susan’s Fish-n-Chips. While this joint certainly specializes in classic fish and chips, you can also enjoy some amazing fried clams. Pair the clams with an order of Susan’s onion rings for a delicious — and extremely filling — meal. When it comes to sampling seafood in Portland, Maine, this casual setting is a great pit stop after a trip to the coast or a hike through the woods.

Bite Into Maine is famous for its Maine clam roll, a delicious sandwich featuring tender fried clams and your choice of seasoning. Or, try the clam dip, a delightful mix of minced clams, sour cream, and cream cheese. The dip is served with Cape Cod potato chips, offering the best conduit for this goodness. Delish!

…And Oysters…

Looking for something fancy? Dive into the oyster scene in Portland with a meal at Street and Co. This upscale restaurant boasts a wide selection of fresh oysters. The quaint atmosphere of the bistro invokes Mediterranean vibes, welcoming you in and beckoning you to stay and order seconds. But be sure to leave room for a piece of Street and Co.’s famous bourbon pecan pie.

No trip to Portland is complete without a trip to J’s Oyster Bar, a restaurant that’s been a mainstay on the scene for over 45 years. This local institution is distinguished for its sweeping views of the waterfront. The oyster menu offers something for nearly everyone. You’ll find traditional raw oysters, oysters baked and stuffed with lobster, oysters Rockefeller, and oysters with a Mornay cheese sauce.

…And Scallops…

Located in a trendy warehouse setting, Fore Street is the perfect spot to indulge in some luscious scallops. Fore Street is an iconic New England dining destination. The wood-burning oven is visible from most tables, creating a cozy atmosphere while you enjoy the beautifully-seasoned seafood. The seasonal menu boasts some of the freshest flavors in the region, making it a favorite for discerning diners.

You also can’t go wrong with the scallops at Scales. This local restaurant is a sister venue to both Fore Street and Street & Co., and the commitment to excellence shows. The seared scallops are a worthy complement to the beautiful water view that you’ll enjoy in the Old Port district.

…And Shrimp…

In addition to delicious scallops, Scales is also known for its myriad shrimp options on the menu. Chief among them is the wood-grilled shrimp served with a variety of seasonal sides. Side dish options include loaded potatoes, roasted eggplant, broccolini, and more.

Boone’s Fish House & Oyster Room is another popular choice for shrimp dishes in the area. Great options include the shrimp scampi or the classic chilled shrimp cocktail. This is an especially great place to visit on a nice day. The double-decker outdoor patios offer amazing views of the harbor, pairing well with a fun happy hour.

You may also like: A Guide to the Historical Side of Portland, Maine

…And Crab!

A converted ferry is home to DiMillo’s on the Water, a lovely restaurant where you can enjoy fresh crab. Here, you’ll find a number of crab specialties, including crab and lobster bisque and crab-stuffed haddock. Start your meal with an order of crab cakes served with ancho lime aioli for a complete crab experience.

For something a little more casual, consider a trip to The King’s Head Pub. This British-style pub offers both a crab roll or traditional crab cakes on the menu. You’ll have your pick of delicious options to enjoy this Portland food specialty. The extensive beer list at this quintessential Old Country pub is just a bonus.

FAQs: 

Q: What are the must-try seafood dishes in Portland, Maine?
A: When visiting Portland, don’t miss out on trying classics like lobster rolls, clam chowder, and fried clams. You can also explore local delicacies like Maine shrimp and seafood stew.

Q: Where can I find the freshest seafood in Portland?
A: For the freshest catch, head to the Portland Fish Exchange, where local fishermen auction their daily haul. Additionally, visit the Old Port area for a variety of seafood restaurants and markets.

Q: What are some family-friendly seafood dining options in Portland?
A: If you’re traveling with family, consider visiting places like DiMillo’s On the Water, Boone’s Fish House & Oyster Room, or Gilbert’s Chowder House. They offer kid-friendly menus and a welcoming atmosphere.

Q: Are there any vegan or vegetarian seafood alternatives in Portland?
A: Yes, even if you don’t eat seafood, you can still enjoy the flavors of the sea with plant-based alternatives. Look for restaurants that offer vegan seafood dishes like “lobster” rolls made from heart of palm or crispy seaweed snacks.

Q: Can I purchase fresh seafood to take home with me?
A: Absolutely! Portland boasts several seafood markets like Harbor Fish Market and Browne Trading Company, where you can buy fresh seafood to cook at home or have it shipped to your door.

Q: What’s the best time of year to visit Portland for seafood lovers?
A: While seafood is available year-round in Portland, the peak season for lobster is from June to September. If you’re a lobster enthusiast, plan your visit during these months for the most abundant and affordable options.

Q: Are there any seafood festivals or events in Portland that I should check out?
A: Yes, keep an eye out for the Maine Lobster Festival in nearby Rockland, which usually takes place in August. It’s a fantastic opportunity to indulge in various lobster dishes and enjoy live entertainment. Additionally, Portland hosts the annual Portland Seafood & Wine Festival, typically in February, showcasing the region’s finest seafood and wines.

Have you been to Portland, Maine? Tell us what you did on your trip in the comments below!