If you’re looking for a hidden gem that’s perfect for New England leaf-peeping this fall not far from Boston or NYC, Portland, Maine should be top of your list. The quaint waterfront town’s explosions of red, orange, and purple leaves peppering lighthouse-covered rocky shorelines will lure you in — while its incredible dining, art, and shopping scenes will make it an unforgettable trip. 

With some of the best lobster rolls in the region (and, ahem, the world), and local artists, makers, and venues giving their all, it’s the quintessential weekend trip. But what should you do on a perfect fall weekend in the East Coast’s Portland? Even if you’re not a nature lover looking to hike or bike, there’s still plenty to do — here are our best recommendations. 

Where to Stay in Portland

The Weldon Hotel

Newly opened in August in the Old Port neighborhood just blocks from the waterfront, The Weldon Hotel should be top of mind for any traveler looking for a boutique experience with a whole lot of space. The brick-walled luxury hotel is surrounded by the best shopping and dining the city has to offer, with deluxe suites where you can work, cook, do laundry, work out, and make the most of your stay. 

Canopy Portland Waterfront

As you can see by the gorgeous rooftop views, the downtown Canopy Portland Waterfront is a great choice for luxe amenities and waterfront overlooks. The best part? Luna Rooftop Bar, a picturesque spot for a locally-sourced cocktail and a bite before a night on the town.

Where to Eat in Portland

Luke’s Lobster Portland Pier

Once you’ve settled into your hotel, your first stop should probably be Luke’s Lobster Portland Pier for the best lobster rolls in the city (and so much more!). Located on the pier seated above the water, the two-story restaurant offers incredible views, a heartwarming family story, and even better food. 

Ocotillo

For brunch, head to Ocotillo in the West End for a Tex-Mex BBQ fusion meal filled with empanadas, burgers, tortas, tacos, salads, bowls, and more in bright, trendy digs. Whatever you do, don’t miss out on the churros dusted with cinnamon sugar alongside a number of fruity and chocolatey dipping sauces. 

What to Do

Aside from eating all the seasonal seafood you can handle and admiring the stunning foliage and waterfront views, you can’t miss out on the shopping. Portland’s ultra-walkable budding retail scene winds along cobblestone streets from Viand Mercantile for all things home and beyond, to the Cheese Shop of Portland for the region’s best wines, cheeses, meats, and olive oils for the fall picnic of your dreams.

Take a “Cannabis Vacation”

Did you know that Portland is considered the cannabis capital of the East Coast with dozens of recreational and medical marijuana shops? For visitors over 21, stop by the brand-new, first-of-its-kind women-owned microdosed cannabis shop, Pot + Pan, in the ultra-hip Woodfords neighborhood for THC- and CBD-infused gummies, bonbons, cakes, chocolate bars, and other baked goods (including their special-edition fall flavors, like the pumpkin spice latte bar). Plus, they also sell adorable kitchen gear! Sweet tooths will want to finish off the trip with can’t-miss (non-THC) baked treats from Two Fat Cats, a local bakery opening its second Portland location this October.

Want to explore more of New England this fall? Check out our guide to the best fall road trips!