A first-time guide to Portland, Maine

31.07.2024 - 16:44 / lonelyplanet.com

Jul 30, 2024 • 8 min read

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.

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.

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