A first-time guide to Portland, Maine

Combining rugged beauty, maritime history and a thriving culinary scene, the city of Portland is one of Maine’s shining stars, showcasing the best of New England.

Situated on Casco Bay, Portland packs a punch across its walkable Old Port district, beautiful working waterfront and historic neighborhoods – and there’s a lot to explore. This small city (even though it’s the largest in the state) is a destination where you can sip craft cocktails in a t-shirt or flannel without judgment, or walk into a dive bar and become friends with some locals over blueberry-pie Jell-O shots (more on that below).

If eating the best lobster roll you’ve ever had at a lighthouse perched on the Atlantic Ocean sounds like your kind of thing, Portland is for you. And while lobster and ocean views are the city’s calling cards, there’s much more to discover here.

Outdoor activities get you pumped up? Lace up your boots to take to the numerous hiking trails nearby. Love the beach? Portland has you covered. Looking for culture? Check out the buzzing art scene. If you’re looking for a weekend of superb eating and drinking, or a few days of wellness, Portland can provide whatever kind of escape you want. It’s a place that encapsulates Maine’s tagline, “The way life should be.”

Relaxed, friendly and fun, Portland never disappoints. If you’re planning your first trip, here’s all you need to know.

When should I go to Portland?

Summer is peak season for Portland (and for Maine), with warmer temperatures ideal for taking advantage of all outdoor pursuits, taking a dip in the chilly ocean and spending Thursday or Friday evenings washing down food-truck fare with local brews, your foot tapping to live music at Thompson’s Point – for free. While summertime is spectacular in southern Maine, it’s also a very popular time to visit, so expect many fellow visitors and higher prices for accommodations. Portland Wine Week in June is an especially busy time.

Portland charms in all seasons – though the weather does turn frigid and snowy in the winter. Yet the snowflakes falling on the cobblestone streets of the Old Port are fetching indeed, and you can always get cozy with a hot toddy in one of the city’s many tucked-away cocktail bars.

The shoulder season in Portland may be the sweet spot, with fewer crowds and more budget-friendly accommodation come fall and spring. Leaf-peepers can enjoy the colorful display anywhere from mid-September to the end of October. Foodies will savor the annual Harvest on the Harbor festival, held in late October or early November.

How much time should I spend in Portland?

The destination works well as a weekend escape – in a couple of days, you can sample a couple of restaurants, breweries and museums – though three to four days will spare you feeling rushed while providing a full taste of the city. You can cover the essentials and tack on a local hike, a sunset sailing trip in Casco Bay or an afternoon perusing local boutiques. However long you visit Portland, consider it recon for your next trip. You’ll want to come back.

Is it easy to get in and around Portland?

We recommend taking a car to Portland for maximum freedom and flexibility. Street parking can be tricky downtown, and in the Old Port; there are a few paid parking garages. I always find a spot if I’m willing to walk a few blocks – just be prepared to circle around a few times.

Portland International Jetport lies just 2 miles from downtown. Alternatively, it’s possible to fly into Boston Logan International Airport and rent a car for the almost 2-hour drive north. Amtrak trains reach Portland at Thompson’s Point, just a touch west of the city: the Downeaster travels along the coast every day south to Boston and north to Brunswick.

With the Old Port as your base, you can easily walk to many popular attractions and restaurants. (It’s wise to seek out accommodation that offers parking, especially in the summer.) Public transport is available for those without a car, thanks to Greater Portland METRO.

Top things to do in Portland

Eat, eat – and eat some more

Portland has earned its reputation as a gourmet’s paradise. Classic diners serve delicious comfort food like pancakes with wild Maine blueberries, while chefs of the highest caliber put their impressive mark on a range of cuisines.

Anyone arriving hungry in Portland will want to start with a lobster roll. A deeper dive will unearth everything from craft donuts to Southern barbecue; Greek, Asian, Mexican and Puerto Rican joints; food trucks; and much, much more.

If you like oysters, sampling treasures freshly plucked from the Atlantic is a must. You can’t go wrong at The Shop by Island Creek Oysters in the East Bayside neighborhood, which has a lively atmosphere and killer Bloody Mary. (Yes, it’s topped with an oyster.)

Portland is known for its buzzing breweries and craft cocktail bars. On the sprawling patio at the city’s most famous brewery, Allagash Brewing Company, you can down another lobster roll from the Bite Into Maine food truck. First-timers shouldn’t skip the hot and crisp hand-cut Belgian frites at Duckfat – a true Portland institution, whose cones of twice-fried duck-fat fries live up to the hype.

Hop aboard a boat

The ruggedly handsome coast begs to be explored, and the perspective from the water is superb. I love the Wine Wise wine sails in the late afternoon or evening for sunset.

Visit at least one lighthouse

Head south to Cape Elizabeth to take in the historic and still-operating Portland Head Light, which dates to 1791. Check out the on-site museum and wander the trail for different viewpoints of the extremely photogenic lighthouse. If you happen to visit on Maine Open Lighthouse Day, you’ll be one of the lucky guests to climb the tower – it’s open to the public exactly one day a year.

Hit some nearby trails

Stretch your legs and work off those donuts with a nearby hike. The 3.6-mile waterfront Back Cove loop trail features views of the city on the city’s northeastern edge. A 15-minute drive from town lies Mackworth Island, where a short 1.25-mile trail traces the shore of this tiny speck, which is a state park of the same name. Birding enthusiasts will love that it’s an official bird sanctuary, where you might spot osprey and other shorebirds. About half an hour north of Portland by car, Wolfe’s Neck Woods State Park is home to six trails of varying lengths that feature scenic vistas of Casco Bay, Googins Island and the Harraseeket River.

My favorite thing to do in Portland

I can’t get enough of the food and bar scenes in Portland. When I visit, I always return to Central Provisions for the Baja fish sandwich and to Gilbert’s Chowder House for a steamy bowl of New England clam chowder. And I always pepper in a couple of new-to-me restaurants and breweries each time. (There are always new places to try.)

I always make sure to get my donut fix at Hifi Donuts (I love the Mexican Hot Chocolate or Calico Glaze flavors). Come evening, while I can never resist a craft cocktail from stylish Blyth & Burrows on Exchange St, my heart is happier at a dive bar like Dock Fore, which specializes in local banter and those aforementioned blueberry-pie Jell-O shots.

How much money do I need for Portland?

It depends. You can take in Portland on a mid-range budget – or easily ascend to the stratosphere. I’ve found that even a late-night slice of pizza here is pricier than in other places. Yet if you know where to go and are willing to travel outside of peak season, it’s possible to visit without draining your bank account.

If you’re on a budget, focus on free activities like wandering the waterfront, visiting lighthouses and beaches, and hiking nearby trails. Get your lunch at a food truck, freeing up money to spend on dinner and drinks in the evening.

• 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 out for two: $40–75

• Slice of late-night pizza: $4.50–7

• Craft cocktail: $13–20

Frequently asked questions about Portland

How should I pack for Portland?

No matter the season, bring lots of layers. Maine’s weather can be fickle, changing on a dime. The temperature varies quite a bit within the space of one day – think chilly mornings and evenings and hot afternoons in the summer. Year-round, you should always have a rain jacket and windproof layer on hand. In winter, you’ll want to have a solid winter coat and boots, sweaters and thinner wool layers to keep warm and peel off once you’re inside a cozy restaurant.

Do I need to make advance restaurant reservations in Portland?

Yes. Portland is a true foodie hub, and you don’t want to find yourself missing out on a meal at that restaurant on the tippy top of your list. Reserve ahead where you can, especially in peak summer season.

How much should I plan to do in one day or weekend in Portland?

Don’t overprogram yourself. If you’re anything like me, you’ll be tempted to pack in as much as possible on your first trip in order to make the most of your time. Yet I highly recommend forcing yourself to take it a little slower, and truly savor what you are doing, seeing and eating. I always recommend quality over quantity when it comes to travel experiences.