From Poughkeepsie: 5 hours
The perfect size to explore in a weekend, Maine’s biggest city blends the charm of the state’s coastal towns with big-city attractions. The best way to grasp the city’s history is to get out onto Casco Bay. Portland Discovery Land & Sea Tours offers 90-minute boat tours (bundle up; it gets cold) past some of the many islands. Expect plenty of leaf-peeping opportunities, Civil War battle forts, lobster boats, and picture-perfect views of lighthouses, including the famous Portland Head Light. Art buffs will want to visit Portland Museum of Art, whose collection includes works by former Mainer Winslow Homer.
For lunch, Middle Street is home to two of Portland’s most popular restaurants (choose whichever has the shorter wait). At Duckfat, everything from Belgian-style fries to donut holes rolled in citrus sugar are fried in its namesake elixir, while a dozen types of Maine oysters challenge the brown-butter lobster roll — arguably the city’s best — for seafood supremacy at Eventide Oyster Co. After, indulge your sweet tooth with a chewy, walnut-studded, chocolate-rye cookie at Standard Baking Co. For dinner, don’t even think about skipping Central Provisions. Nab an early-bird seat at the counter to watch your meal being prepared right in front of you.
(L to R) The Holy Donut; Eventide Oyster Co. by Zack Bowen
Stop into Folly 101 to peruse the pretty, color-coded dinnerware before trying the legendary mashed-potato donuts at The Holy Donut. Or skip the hype and head to Becky’s Diner for runny eggs served over homemade corned beef hash. On your way out of town, don’t miss the chance to try whatever Belgian-style beers are on tap at Allagash Brewing Company. Did we mention tastings are free?
STAY: The Press Hotel
Since opening in 2015, this boutique hotel — in the former Portland Press Herald building — has garnered nearly constant buzz from media outlets. Maybe it has something to do with our weakness for its tongue-in-cheek vintage-writer’s décor (an art installation of antique typewriters in the lobby, quotes from stories wallpapering the halls). But even if you’re not part of the media, there’s plenty to love about The Press Hotel, starting with its center-of-town location. The 110 rooms feature oversize windows, Frette linens (plus chocolates at turndown service!), and large marble-tiled bathrooms with oversized rain-head showers and Bigelow bath products. Just off the lobby, UNION restaurant (Josh Berry was named Chef of the Year by the Maine Restaurant Association in 2017) serves cocktails and locally sourced dishes, including a smoky charcuterie plate and bucatini with chili-cured egg yolk, lemon, and mizuna. From $299/night; www.thepresshotel.com