The Ultimate Insider’s Guide
Portland, Maine, Beyond the Lobster: The Insider's Guide
By Bhavana Scalia-Bruce
Portland, Maine, is rapidly earning its reputation as a culinary hotspot, especially in the seafood department. However, this vibrant New England city on Casco Bay offers much more than lobster and chowder. (Potato donuts, anyone?) Beyond its famed dishes, Portland boasts Victorian-era architecture, outdoor adventures, museums, minor league baseball, and offshore islands. It's the perfect summer getaway—and this is how we do it.
Indulge Your Inner Foodie
Commercial Street, located in the heart of the waterfront downtown, is the heart of the foodie scene in Portland, and is brimming with foodie-favorite restaurants, stylish bars, and quintessential New England Experiences.
Come morning, your first stop should be the Holy Donut. This beloved spot offers a twist on the treat, crafting its donuts with Maine-based potatoes, which gives them a delicious dense yet fluffy texture. If you’re looking to embrace that classic diner atmosphere, head down to Becky's Diner, where, if you’re up early enough, you can tuck into classic eggs and pancakes alongside local fisherman.
For delicious meals with an ocean view, book your table at Flatbread Pizza Co., ThePorthole, Boone's Fish House & Oyster Room, or the Portland Lobster Company, each offering excellent dining and regular live music. For the best seafood chowder in town, make your way to Gilbert's Chowder House. Nestled right on the wharf between Bangs Island Mussels and the Harbor Fish Market, this local favorite is a hit among lobstermen, so you know it’s good.
To get even closer to the water, make a reservation at DiMillo's Floating Restaurant—a quintessential dining experience in Portland. Located dockside, the restaurant is housed in a retired car ferry, and serves delicious Main-themed cuisine while providing stunning views of the Portland Harbor.
Additional fine-dining options downtown include Scales restaurant for ultra-fresh seafood, Street and Company for Mediterranean-inspired dishes and cozy vibe on a quaint cobblestone street, and Central Provisions for creative small plates.
Sip Around Town
For a night on the town, head to Wharf Street, which is brimming with bars and breweries, and tucked snugly behind Commercial Street. In the summer, we highly recommend enjoying a cocktail or two at The Independent Ice Co., a fun outdoor fine-whisky bar with a prime location for people-watching.
To find the best rooftop bar in the city, sneak up to the top of the Canopy Hotel and settle into a table at Luna, which is the perfect spot to sip and relax. Brewery enthusiasts will also enjoy Camp Pennant on Commercial Street with a wide selection of brews and cocktails. And those thirsty for some real local flavor, head to Lincolns Speakeasy, tucked away on Market Street. Pro tip: Bring cash, as most drinks set you back a Lincoln.
Out and About
Don't miss a leisurely day exploring Portland's Old Port. It's packed with gift shops, boutiques, bookstores, breweries, bars, and restaurants. This is also where you can hop on one of Portland Discovery Land and Sea Tours Old-fashioned trolleys, which is a great way to make sure you’ve hit all of the city’s highlights.
To further immerse yourself into Portland's history and culture, make your way to the Portland Observatoryand Portland Museum of Art. The observatory offers breathtaking panoramic views and insights into the city's maritime past, while the museum, in Portland’s Arts District, showcases its diverse collection of contemporary and classical artwork. It is also worth carving out a few hours to tour Portland’s Victoria Mansion for a glimpse into 19th-century opulence, and the city’s rich history. The Italianate villa, which was built in 1858, preserved interiors showcasing its grandeur of the Gilded Age.
Set Out Island Hopping
The state of Maine has over 4,600 islands off its coast. Spend an afternoon exploring just a few of them by hopping on a sailboat cruise or a booze cruise around Casco Bay with Portland Schooner Co. Casco Bay Linesalso offers rides to seven islands, including a 20-minute ferry ride from Commercial Street to Peak's Island, a favorite among locals. The island is perfect for a leisurely exploration, whether you’re biking around or renting a golf cart from Mike’s Carts, followed by a relaxing lunch atTheInn on Peaks Island.
Family Fun
For a night of family fun, swing over to a Portland Sea Dogs game. Maine's minor league team is affiliated with the Boston Red Sox. Located in the heart of Portland, Hadlock Field is a destination for fans of all ages to root for the home team. Whether you're a baseball die-hard or just looking for a fun night out, you’ll find a Sea Dogs game to be a home run.
Road Tripping to Portland?
No trip to Maine is complete without making a stop in one of Portland’s neighboring towns. Wells, Kennebunk, Kennebunkport, or Ogunquit, which are equally enchanting, line the coast with quaint local boutiques specializing in coastal-themed jewelry, local crafts, and art.
Approximately 20 minutes from downtown Portland, Cape Elizabeth is one of the must hit towns in the area. Here, you can take a scenic walk at Portland Head Light/Fort Williams Park, home to the world’s most photographed lighthouse, and stop by local favorite The Lobster Shack at Two Lights for some of the best lobster rolls in the state with a picturesque view.
A little further afield, Kennebunkport, famously home to the Bush family, exudes an air of elegance, whereas Kennebunk offers a more laid-back, rustic feel. The neighboring towns are home to beaches, vibrant maritime history with the Seashore Trolley Museum, and oceanfront activities from kayaking and paddleboarding.
Old Orchard Beach, also just 20 minutes outside the city, is another family-friendly stop. It's home to The Pier and Palace Playland, an oceanfront amusement park with a carnival-like atmosphere. Don’t miss a ride on its ferris wheel for views of endless waves and the town as a thrilling finale to your New England getaway.
