Do you need travel tips for exploring Portland, Maine? With its expansive rocky coastline, charming seaside towns, and of course, the state’s most popular delicacy, the lobsta’, Maine has an almost mystical status.
Exploring this picturesque state on a boomer road trip is a great way to see Maine’s charming seaside towns, but when it comes to visiting Portland, make sure to include plenty of time to explore properly. Guest contributor, Candi Licence from Candi and Michael on the Move, is here with some useful travel tips for a Portland, Maine vacation.
Portland’s, combination of natural coastal beauty, funky personality, excellent dining choices, and artsy vibe makes it an attractive destination. Yet, the city also retains its strong working roots as the largest tonnage port in New England and closest ice-free port to Europe.
Located on southern Maine’s rugged, rocky coast and less than 2 hours from Boston, Portland can be explored over a long weekend. It includes big city attractions like museums, opera, and ballet. While parks, hiking trails, and nearby islands make Portland an attractive destination for nature lovers as well.
Table of Contents
Spend a long weekend in Portland, Maine
Portland’s confined peninsula location forces it to be a compact, walkable city. The variety of excellent shopping and dining experiences makes it hard to narrow down your preferred top choices.
You will find yourself lured into small shops bursting with unexpected treasures. Or you may detour down colorful cobblestone side streets as you try to reach your planned destination.
Boomer Travel Tip
Looking for a place to stay in Portland? Start your search for where to stay in Portland, Maine with us!
This New England seaport embraces its history but also has a youthful, edgy feel due to the many young entrepreneurs creating businesses here. Portland appeals to everyone from nature lovers to sophisticated, discerning day trippers and savvy foodie travelers.
Discover Portland’s art and culture scene
The Portland Art Museum, acclaimed as the best regional museum in the country, engages visitors with thought-provoking exhibitions. The Institute of Contemporary Art, part of the Maine College of Art, features innovative exhibitions and public programs that showcase new perspectives and trends in contemporary art.
You can easily sample a wide variety of art from avant-garde and traditional sculpture and paintings, to jewelry and fine crafts in over 25 galleries clustered within a 14-block arts district.
Portland proudly supports eight museums and ten performing arts centers. Portland Stage produces off-Broadway shows.
You can see excellent performances at The Portland Ballet Company, Opera Maine and The Portland Symphony Orchestra. Several theater groups and improv companies delight patrons with their plays and comedies.
You’ll find one of the best examples of Italian Villa Style architecture in the United States at Victoria Mansion. A New Orleans hotel baron built the mansion in the late 1850s as a summer home.
The mansion’s ornate furniture, gilded rooms, and fine art showcase the opulence and elegance of the era. Take time to study the 6-by-25-foot stained-glass ceiling window, trompe l’oeil walls, and ceilings. With over 90% of the original furnishings restored and on display, you can see and feel how the one percent lived in the mid-19th century.
Dining in Portland
Portland’s competitive dining scene highlights fresh, local produce, meat, and seafood delivered daily. The seaside city boasts the nation’s most culinary establishments per person (1 restaurant for every 104 people). In 2018, Bon Appetit Magazine named Portland the Restaurant City of the Year.
Visitors enjoy 360 dining choices ranging from humble but delicious potato flour donuts at The Holy Donut (consistently rated one of the best donut shops in the country), to laid back Parisian fare at Petit Jaqueline and Pan Asian/Vegetarian delicacies at The Green Elephant. Or savor excellent local cuisine at David’s, J’s Oyster, The Grill Room and Bar, and Fore Street.
Can’t decide where to eat? Try one of Portland’s foodie tours (Maine Foodie Tours and Maine Food for Thought) for curated delicacies and insider information about the restaurants and where their food is sourced.
Craft Brewing and Distilling
For a great brew, don’t miss Allagash Brewing Company making Belgian inspired beer and recent winner of the 2019 James Beard Award for Outstanding Wine, Spirits, or Beer Producer. Or try Rising Tide Brewing Company, a family-owned brewery specializing in small batch, specialty ales.
Shipyard Brewing Company, Maine’s largest brewer, is one of seven breweries conveniently located in town. Over 20 craft breweries, many award-winning, call the greater Portland area home.
If Spirits are more to your liking, try New England Distilling. Portland’s first distillery since Prohibition produces premium small batch spirits using local ingredients.
Another favorite, Hardshore Distilling Company, strives to create new flavors, including its flagship product, Hardshore Original Gin. Produced in small batches, the botanicals in Hardshore Gin create subtle flavor changes as you roll the gin in your mouth.
Brewery tours highlight the best of Portland’s offerings. Take one of the Maine Brew Bus tours to visit a variety of breweries, wineries and/or distilleries without driving. Their catchy motto is ‘Driving You to Drink Local.’
Where to eat lobster in Portland, ME
Ah, Lobster. Maine’s signature specialty can be sampled in eateries from modest fish shacks to the most elegant dining venues. Delight in finding your favorite lobster joint, often the highlight and obsession of many vacationers.
Chefs prepare just caught lobster and seafood in styles from simple to sublime. Five James Beard award-winning chefs create exciting new dishes, and several Beard nominees diligently strive to earn this honor in the coming years.
Locals’ favorite places to eat lobster include Eventide Oyster Co. for the city’s freshest raw bar as well as their famous lobster roll using browned butter that gives it a nutty taste and Portland Lobster Company located right on the waterfront. Splurge at DeMillo’s On the Water or at Street and Co.
Or, for a different lobster experience, board Lucky Catch Cruises to watch or join a lobster boat crew haul their daily catch and purchase their bounty at a discount.
Portland’s History
Did you know that during World War II, Portland was the US North American fleet’s home port? The Liberty Ship Memorial recounts Portland’s legacy as a significant shipbuilding facility and the importance these ships served, supporting the Allied effort to win the war.
See panoramic views of the sea, coastline, and mainland from the Portland Observatory. Former sea captain turned entrepreneur, Lemuel Moody, built the 86 foot tall tower allowing him to see 30 miles out to sea.
Ship owners who paid Moody a $5 annual fee, saw their signal flags hoisted three days before their ship came into view of the port. The tower gave those ship owners a competitive advantage and streamlined the efficiency of the harbor. America’s last maritime signal tower still stands, offers tours and the best views in the city.
The Portland Freedom Trail, a self-guided tour, commemorates sixteen abolitionists landmarks associated with the Underground Railroad. Pick up a map and explore Portland’s connection and contribution to the Underground Railroad.
The excellent Old Port Historic Walking Tour delivers an insiders view of the city and highlights significant landmarks, statues, and architecture of the city. It can be taken as a regular walking tour or as a jogging tour with a short workout added at each stop. And the tour provides an informative way to work off some of the calories you have consumed.
The Casco Bay Islands and Lighthouses
Twelve major and 96 minor islands dot Casco Bay, along greater Portland’s coast. Get out on the water and explore the jagged coast, neighboring islands, and lighthouses. A Maine Windjammer Cruise in Penobscot Bay is another great option.
Options include an elegant Schooner sail, boats for hire, kayaks, the Casco Ferry Lines or hop on America’s longest operating mailboat. Portland and the surrounding areas have beautiful beaches.
Five lighthouses protect Portland’s harbor. Cape Elizabeth’s 8th century iconic Portland Head Light stands proudly at the mouth of the harbor 129 feet above sea level and is one of the most photographed lighthouses in the world. In contrast, the smallest lighthouse, nicknamed The Bug Light, stands only 26 feet tall and looks like a tiny ancient Greek monument.
Why travel to Portland?
Portland’s entrepreneurial spirit and large number of cultural attractions erase its reputation as a sleepy, forgotten coastal city. Worldwide Business Insider rates Portland as the #3 Place to Visit. Women own 30% of the local businesses. Travel + Leisure ranked Portland the #9 best city for Hipsters and #6 for ice cream.
Additional accolades include Best Small Cities in the US by National Geographic, Regions on the Rise by Time Magazine, Top Ten Kid-friendly Cities in the Country, Top Spot for Business by Forbes, and one of America’s Happiest & Healthiest Cities by Inc.
As the original capital of Maine (and its largest city) plus its relative proximity to Boston (under 2 hours) makes Portland a natural getaway destination. Portland contrasts an enticing mix of old and new, funk and sophistication, historical and fresh. “Authentic ~ by Nature,” Portland Maine invites visitors to walk the city and appreciate the art, culture, architecture, food, and drink.
Tips for Visiting Portland, Maine
- Contact Visit Portland Maine, and request an extensive electronic or printed brochure that highlights Portland’s attractions.
- Portland features 50+ festivals each year, including music, wine, birding, sailing, lobster, ethnic, garden, Christmas, paddle sports, and Bach festivals. Plan your trip around your favorite festival.
- Four miles from the Portland Airport and 2.5 miles from the Amtrak station, a taxi or Uber will deliver you to the city quickly and inexpensively. Once you’ve arrived, walking is the best, and most fun option. Walkscore.com rates downtown Portland a ‘walker’s paradise’ with a score of 96 out of 100. Most attractions are within a 1-2 mile walk.
- Maine celebrates its bicentennial in 2020. Be sure to check out its calendar of events and celebrations at Visit Portland.
- Add a 2-day Acadia National Park itinerary to your trip. It’s only 3 hours from Portland!
Save to Pinterest
