A Beginner's Guide to Portland, Maine

Blending stunning landscapes, rich maritime heritage, and a vibrant food scene, Portland shines as one of Maine’s top destinations, showcasing the essence of New England.

Nestled along Casco Bay, Portland offers an exciting mix within its walkable Old Port district, picturesque working waterfront, and historic neighborhoods—there’s so much to see. This small city, the largest in the state, is the perfect spot to enjoy craft cocktails in casual attire or strike up a conversation with locals at a dive bar over unique treats like blueberry-pie Jell-O shots (more on that later).

If savoring the freshest lobster roll at a lighthouse overlooking the Atlantic sounds appealing, then Portland is your place. While lobster and stunning ocean vistas are highlights, there’s so much more to uncover in this city.

Are outdoor adventures your thing? Put on your hiking boots and hit the many trails nearby. Enjoying beach time? Portland has plenty to offer. Interested in the arts? Don’t miss the lively art scene. Whether you’re after a weekend filled with delicious dining and drinks or a few days dedicated to wellness, Portland has the perfect escape for you. It truly embodies Maine’s motto, “The way life should be.”

Charming, welcoming, and enjoyable, Portland always exceeds expectations. If you’re getting ready for your first visit, here’s everything you need to know.

When is the best time to visit Portland?

Summer is the peak season for Portland (and for Maine), offering warm temperatures perfect for outdoor activities, refreshing swims in the cool ocean, and spending Thursday or Friday evenings savoring food truck delights paired with local brews, all while enjoying live music at Thompson’s Point—at no cost. While summer in southern Maine is stunning, it’s also a highly sought-after time to visit, so anticipate crowds and higher accommodation rates. Portland Wine Week in June is particularly bustling.

Portland enchants throughout the year, though winters can be quite cold and snowy. Still, the sight of snowflakes drifting down on the cobblestone streets of the Old Port is truly picturesque, and you can always warm up with a hot toddy in one of the city’s cozy cocktail bars.

The shoulder seasons in Portland might be the best time to visit, offering fewer crowds and more affordable accommodations during the fall and spring. Leaf-peepers can revel in the vibrant foliage from mid-September to late October. Food enthusiasts will love the annual Harvest on the Harbor festival, which takes place in late October or early November.

How long should I plan to stay in Portland?

Portland makes for an ideal weekend getaway—just a couple of days allows you to sample various restaurants, breweries, and museums. However, spending three to four days gives you a more relaxed experience, letting you fully explore the city. You can check off the highlights and add in a local hike, a sunset sailing adventure in Casco Bay, or an afternoon of shopping at local boutiques. No matter how long your stay, think of it as a reconnaissance mission for your next visit—you'll definitely want to return.

Is it convenient to navigate Portland?

For the greatest freedom and flexibility, we suggest driving to Portland. Finding street parking can be challenging in the downtown and Old Port areas, although there are a few paid parking garages available. I usually manage to find a spot if I'm willing to walk a bit—just be ready to drive around a few times.

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

With the Old Port as your starting point, you can easily stroll to many of the city's popular attractions and dining spots. (It's a good idea to find accommodations with parking, especially during the summer.) For those without a car, public transportation is provided by Greater Portland METRO.

Must-Do Activities in Portland

Indulge in delicious eats—again and again

Portland has rightfully earned its status as a food lover’s paradise. Classic diners serve up comforting dishes like pancakes topped with wild Maine blueberries, while top-notch chefs showcase their skills across various cuisines.

Anyone arriving in Portland with an appetite should definitely start with a lobster roll. A deeper exploration reveals an array of delights, from craft donuts to Southern barbecue, and eateries serving Greek, Asian, Mexican, and Puerto Rican cuisine, along with food trucks and much more.

If you’re a fan of oysters, you must try the treasures freshly harvested from the Atlantic. You can’t go wrong at The Shop by Island Creek Oysters in the East Bayside neighborhood, known for its vibrant atmosphere and excellent Bloody Mary—yes, it comes topped with an oyster.

Portland boasts a lively scene of breweries and craft cocktail bars. At the sprawling patio of the city's renowned Allagash Brewing Company, you can enjoy another lobster roll from the Bite Into Maine food truck. First-timers shouldn’t miss the hot, crispy hand-cut Belgian frites at Duckfat—a true Portland staple, where the twice-fried duck-fat fries live up to the reputation.

Take a Boat Ride

The ruggedly beautiful coastline invites exploration, and the view from the water is exceptional. I particularly enjoy the Wine Wise wine sails in the late afternoon or evening, especially for sunset.

Make sure to visit at least one lighthouse

Head south to Cape Elizabeth to admire the historic and still-active Portland Head Light, which has stood since 1791. Explore the on-site museum and wander the trails for various picturesque views of this photogenic lighthouse. If you visit on Maine Open Lighthouse Day, you’ll be among the fortunate few to climb the tower—it’s open to the public only one day a year.

Explore some nearby trails

Get moving and burn off those donuts with a nearby hike. The 3.6-mile waterfront Back Cove loop trail offers lovely views of the city along its northeastern edge. Just a 15-minute drive from downtown is Mackworth Island, where a short 1.25-mile trail hugs the shore of this tiny state park. Birdwatchers will appreciate that it’s an official bird sanctuary, where you might see osprey and various shorebirds. About half an hour north of Portland by car, Wolfe’s Neck Woods State Park features six trails of different lengths with stunning views of Casco Bay, Googins Island, and the Harraseeket River.

My favorite activity in Portland

I can’t get enough of the vibrant food and bar scene in Portland. Whenever I visit, I always stop by Central Provisions for their Baja fish sandwich and Gilbert’s Chowder House for a warm bowl of New England clam chowder. I also like to mix in a few new restaurants and breweries each time, as there’s always something new to discover.

I make it a point to satisfy my donut cravings at Hifi Donuts (the Mexican Hot Chocolate and Calico Glaze flavors are my favorites). In the evening, while I can’t resist a craft cocktail from the chic Blyth & Burrows on Exchange St, my heart truly lies with dive bars like Dock Fore, known for its local vibe and those delicious blueberry-pie Jell-O shots.

What’s the budget for visiting Portland?

It varies. You can explore Portland on a mid-range budget or easily splurge significantly. I’ve noticed that even a late-night slice of pizza tends to be pricier here than elsewhere. However, if you know where to go and travel outside of peak season, it’s possible to enjoy your visit without overspending.

If you’re watching your spending, prioritize free activities like strolling the waterfront, exploring lighthouses and beaches, and hiking nearby trails. Grab your lunch from a food truck, which allows you to save up for a nice dinner and drinks later.

• 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 questions about visiting Portland

What should I pack for Portland?

Regardless of the season, bring plenty of layers. Maine’s weather can be unpredictable, shifting quickly. Expect significant temperature changes throughout the day—cool mornings and evenings with warm afternoons in summer. Always keep a rain jacket and windproof layer handy. In winter, ensure you have a sturdy winter coat, boots, sweaters, and lighter wool layers to stay warm while being able to adjust when you step into a cozy restaurant.

Should I book restaurant reservations in advance for my trip to Portland?

Absolutely. Portland is a genuine foodie paradise, and you don’t want to miss out on dining at your top-choice restaurant. Be sure to make reservations where possible, especially during the busy summer months.

What’s a reasonable amount to plan for one day or a weekend in Portland?

Avoid overloading your schedule. If you’re like me, you might feel the urge to cram in as many activities as possible on your first visit to maximize your time. However, I highly suggest taking a slower pace and genuinely enjoying what you’re doing, seeing, and tasting. I always prioritize quality over quantity when it comes to travel experiences.