A First-Time Visitor's Guide to Portland, Maine

With its rugged charm, rich maritime history, and vibrant food scene, the city of Portland shines as one of Maine’s gems, representing the best of New England.

Nestled on Casco Bay, Portland offers a delightful experience through its walkable Old Port district, picturesque working waterfront, and historic neighborhoods—there’s plenty to discover. This small city (the largest in the state) invites you to enjoy craft cocktails in a t-shirt or flannel without a second thought, or to pop into a dive bar and bond with locals over blueberry-pie Jell-O shots (more on that later).

If indulging in the best lobster roll while overlooking the Atlantic at a lighthouse sounds appealing, Portland is your destination. While lobster and scenic views are the city’s highlights, there’s so much more to uncover.

Are outdoor activities your jam? Put on your hiking boots and explore the many nearby trails. Beach lover? Portland has you covered. Interested in culture? Dive into the vibrant art scene. Whether you're after a weekend of amazing food and drinks or a few days of relaxation, Portland can deliver the escape you crave. It truly embodies Maine’s motto: “The way life should be.”

Casual, welcoming, and enjoyable, Portland always delivers. If you’re gearing up for your first visit, here’s everything you need to know.

When is the best time to visit Portland?

Summer marks the peak season in Portland (and across Maine), with warm temperatures perfect for outdoor activities, cooling off in the chilly ocean, and enjoying Thursday or Friday evenings savoring food-truck delicacies paired with local brews, all while listening to live music at Thompson’s Point—for free. Although summer is breathtaking in southern Maine, it’s also a very popular time, so be prepared for crowds and higher accommodation rates. Portland Wine Week in June is particularly bustling.

Portland enchants in every season—though winters can be quite cold and snowy. The sight of snowflakes dancing on the cobblestone streets of the Old Port is truly beautiful, and you can always warm up with a hot toddy at one of the city’s cozy cocktail bars.

The shoulder season in Portland might just be the ideal time to visit, with fewer crowds and more affordable accommodations in the fall and spring. Leaf-peepers can revel in the stunning colors from mid-September to the end of October, while food lovers can enjoy the annual Harvest on the Harbor festival, typically held in late October or early November.

How long should I stay in Portland?

Portland is perfect for a weekend getaway—just a couple of days is enough to sample several restaurants, breweries, and museums. However, spending three to four days allows you to fully experience the city without feeling rushed. You can check off the must-sees and add a local hike, a sunset sailing adventure in Casco Bay, or an afternoon of shopping in local boutiques. No matter how long you stay, think of it as a scouting trip for your next visit—you'll want to return.

Is getting around Portland easy?

We suggest driving to Portland for the most freedom and flexibility. Downtown and the Old Port can have tricky street parking, but there are a few paid garages available. I usually find a spot if I'm willing to walk a few blocks—just be ready to circle a few times.

Portland International Jetport is only 2 miles from downtown. Alternatively, you can fly into Boston Logan International Airport and rent a car for the nearly two-hour drive north. Amtrak trains arrive at Thompson’s Point, just west of the city: the Downeaster operates daily along the coast, heading south to Boston and north to Brunswick.

With the Old Port as your hub, many popular attractions and restaurants are easily reachable on foot. (It's wise to choose accommodations with parking, especially in summer.) For those without a car, public transport is accessible through Greater Portland METRO.

Must-See Attractions in Portland

Indulge in food—lots of it!

Portland has rightfully earned its status as a food lover's haven. Classic diners dish out comforting meals like pancakes topped with wild Maine blueberries, while top-tier chefs leave their unique imprint on a variety of cuisines.

Anyone arriving in Portland with an appetite should kick things off with a lobster roll. A closer look reveals a treasure trove of options, from craft donuts to Southern barbecue, Greek, Asian, Mexican, and Puerto Rican eateries, food trucks, and much more.

If you're a fan of oysters, you must try the fresh catches from the Atlantic. You can’t miss The Shop by Island Creek Oysters in the East Bayside neighborhood, known for its vibrant atmosphere and amazing Bloody Mary (complete with an oyster on top!).

Portland is celebrated for its lively breweries and craft cocktail lounges. At the renowned Allagash Brewing Company, you can enjoy another lobster roll from the Bite Into Maine food truck on their spacious patio. Don't miss the hot, crispy hand-cut Belgian fries at Duckfat—a beloved Portland staple known for its twice-fried duck-fat fries that truly live up to the acclaim.

Take to the water

The stunning coastline invites exploration, and the views from the water are incredible. I highly recommend the Wine Wise wine sails in the late afternoon or evening for a beautiful sunset experience.

Make sure to visit at least one lighthouse

Journey south to Cape Elizabeth to explore the historic and still-active Portland Head Light, established in 1791. Don't miss the on-site museum and the winding trails offering various scenic views of this photogenic lighthouse. If you're fortunate enough to visit on Maine Open Lighthouse Day, you'll have the unique opportunity to climb the tower, which is open to the public just once a year.

Explore some nearby trails

Burn off those donuts with a nearby hike. The 3.6-mile Back Cove loop trail offers stunning views of the city along its northeastern edge. Just a 15-minute drive from downtown is Mackworth Island, featuring a short 1.25-mile trail that follows the shore of this small state park. Birdwatchers will appreciate its status as a bird sanctuary, where you might see osprey and other shorebirds. About a half-hour drive north of Portland, Wolfe’s Neck Woods State Park boasts six trails of varying lengths with picturesque views of Casco Bay, Googins Island, and the Harraseeket River.

What I love most about Portland

I can’t get enough of Portland’s vibrant food and bar scenes. Whenever I visit, I always stop by Central Provisions for the Baja fish sandwich and Gilbert’s Chowder House for a comforting bowl of New England clam chowder. I also make it a point to try out a few new restaurants and breweries each time, as there are always exciting new spots to discover.

I never miss my donut fix at Hifi Donuts, especially the Mexican Hot Chocolate or Calico Glaze flavors. In the evenings, while I love a craft cocktail from the chic Blyth & Burrows on Exchange St, my heart is truly happier at a dive bar like Dock Fore, known for its local charm and those delightful blueberry-pie Jell-O shots.

What is the estimated budget for a trip to Portland?

It varies. You can experience Portland on a moderate budget or splurge without limits. I've noticed even a late-night pizza slice costs more here than elsewhere. However, if you know where to find deals and avoid peak times, you can enjoy your visit without breaking the bank.

If you're watching your spending, prioritize free activities like strolling along the waterfront, exploring lighthouses and beaches, and hiking local trails. Grab lunch from a food truck to save money for dinner and drinks later on.

• Basic room for two: $200–500
• Self-catering apartments: $170–720
• Luxury hotel: $500–700
• Ferry ticket: $7.20/$14 (off-peak/peak)
• Bus ticket: $2–5 (single ride)
• Coffee: $2.50–6
• Donuts or pastries: $2.75–8
• Brewery beer: $7–9 (pint); $10–16 (flight)
• Lobster roll: $17–38
• Mid-range dinner for two: $40–75
• Slice of late-night pizza: $4.50–7
• Craft cocktail: $13–20

Common inquiries about Portland

What should I pack for Portland?

Regardless of the season, pack plenty of layers. Maine’s weather can change rapidly, often fluctuating throughout the day—expect cool mornings and evenings alongside warm summer afternoons. Always have a rain jacket and a windbreaker handy. In winter, make sure to bring a good winter coat, boots, sweaters, and lighter wool layers that you can remove when you step into a warm restaurant.

Should I book restaurant reservations in advance when visiting Portland?

Absolutely. Portland is a genuine culinary hotspot, and you don’t want to risk missing out on dining at your top-choice restaurant. Be sure to reserve ahead, particularly during the busy summer months.

How much should I aim to do in a day or weekend in Portland?

Avoid over-scheduling your time. If you’re like me, you might be tempted to cram in as many activities as possible on your first visit to maximize your experience. However, I strongly suggest taking a more leisurely approach to fully appreciate what you’re doing, seeing, and tasting. I always advocate for prioritizing quality over quantity in travel experiences.