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
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My family usually takes a big summer trip, but I tore my ACL earlier this year, so we decided to take it slow and allow my body to heal. That said, I also can't stay still, so I decided to plan a trip for my oldest kid and me to visit friends in Los Angeles.
On a recent road trip to Maine from Connecticut, I stopped at Palace Diner, the oldest diner in the state with a reputation for long wait times but a fried chicken sandwich that makes it all worth it.
Wherever I'm headed, near or far, whether it's a two-week trip to Europe or a two-day stay down the shore, I'll always have a pair of comfortable sneakers on my feet (and maybe a second pair in my suitcase). The most comfortable sneakers can make the difference between a perfect travel day spent exploring a new city and a painful afternoon at the hotel with a foot full of blisters.
At the urging of labor activists in the late 19th century, Congress declared a national holiday on the first Monday in September to celebrate the hard workers of the United States. Now, 130 years later, Labor Day has become more widely known as a three-day weekend celebration that officially ends summer. And it's often seen as travelers' last chance to hit the open road, hop on a plane or book a staycation at a nearby hotel to grab one last dose of sunny R&R before the kids go back to school, the days grow shorter and pumpkin spice season begins.
Margaritaville at Sea is expanding its Heroes Sail Free program across its entire fleet to honor first responders, military members, teachers, and others.
Big changes are happening at JetBlue. The Queens-based carrier recently announced it would be pausing or cutting service on two dozen routes, pulling out of seven cities entirely, expanding popular routes on the East Coast, and bringing its much-loved Mint business-class cabin to more domestic routes.