Terri Marshall a RoamRight Blog Author

Rockland, Maine: A Haven For Artists, Heaven For Foodies And Paradise For Sailors

Few places on the East Coast conjure up iconic images the way Maine does. Lighthouses dot the rocky coastline, lobster roll stands line the roads and sailboats cruise through the waters offshore. It’s easy to see why this region inspires artists.

Located on Maine’s Central Coast, the small town of Rockland embodies all of these images. From the boutique hotel 250 Main that showcases work from local artists, to the best breakfast you’ll ever eat in your life at the Home Kitchen Café, Rockland is a quiet little town that will leave you wanting more. And if sailing is on your agenda, a windjammer schooner cruise is waiting for you. Rockland isn’t as well-known as some Maine communities, but it is definitely worth discovering.

Artful Lodging at 250 Main

Overlooking the harbor and within walking distance of the Rockland’s charming restaurants, galleries, museums and shops, 250 Main is an intimate art hotel showcasing the work of local artists. Built to showcase the regions shipbuilding tradition, the hotel features 26 rooms designed for the discerning traveler with unique, reclaimed and industrial décor. Most rooms have water views and it’s worth getting up early to catch the brilliant sunrise over the harbor from the hotel’s rooftop deck.

Be sure to browse each floor to check out the artwork and if you see something you like, you can even make a purchase. It’s also fine to bring along your furry children, 250 Main is pet friendly.

Classic and Contemporary Art on Display

Rockland is home to the famed Farnsworth Art Museum where 20,000 square feet of gallery space displays over 15,000 works of art. The museum is home to an extensive collection of works by the Wyeth family featuring works of Andrew, N.C. and Jamie Wyeth. It’s also home to one of the nation’s largest collections of works by sculptor Louise Nevelson.

Housed in a striking new Toshiko Mori building with an iconic sawtooth roofline, the nearby Center for Maine Contemporary Art Experience displays works by contemporary artists. The CMCA complex includes an ArtLab classroom, gift shop and a courtyard that is open to the public.

Small Town with Big Taste

For a small town, Rockland delivers big when it’s time to eat. Check out the lobster club sandwich at a local favorite, the Brass Compass. The sandwich famously bested Bobby Flay on the Food Network’s "Throwdown with Bobby Flay." Don’t be surprised to find local fisherman hanging out for breakfast and lunch—it’s a Rockland institution. If you’re in the mood for Italian, Rustica delivers traditional Italian dishes with a contemporary flair. The Bacon and Bleu white pizza with caramelized onions is hard to beat.

At the Home Kitchen Café you’ll be spoiled for choice when it comes to breakfast entrees with a variety of "Homelets" traditional breakfasts, pancakes—you name it. Be sure to try the "Sinnies" – cinnamon rolls that are so delicious they’re sinful. And whatever you do, don’t miss the home fries—I recommend adding the onions and peppers.

For the ultimate farm to table experience, head to Primo where the produce is grown on site and the animals are raised on the property. Chef Melissa Kelly has been dazzling guests with her creativity for 17 seasons at this award-winning eatery.

Set Sail on a Windjammer Cruise

Step back to a simpler time aboard the J&E Riggin windjammer. Originally built in 1929 by Charles Riggin, a fisherman who named the ship after his two sons Jacob and Edward, the J&E Riggin began as an oyster schooner. Now a National Historic Landmark, the J&E Riggin is owned by Captain Jon Finger and his wife, Chef-Captain Annie Mahle who offer three, four or six day windjammer cruises.

This is a true sailing vessel with no motor and setting sail from Rockland in the Penobscot Bay, you’ll go where the wind blows you, literally. Besides the rocky shoreline, endless blue horizon and millions of stars overhead at night, a windjammer cruise brings something intangible. There’s a transformation in all who climb aboard.

I joined the boat for the last night of a four-day cruise and it was evident that those already on board had bonded through their experiences. The camaraderie was contagious. Everyone joined in the daily tasks of hoisting the sails, maneuvering into the harbor and helping with the clean-up after the meals.

And speaking of meals, Chef-Captain Annie—an accomplished chef and cookbook author—prepares three healthy and incredibly delicious from-scratch meals daily. This despite the ship having no power and a galley that makes my New York City apartment kitchen look big.

The vessel accommodates up to 24 passengers plus the crew. Space is tight, but that adds to the authenticity of the experience—and no doubt the immediate bonding with other passengers.

Somehow it works for everyone, so much so that many passengers return each year for more time on the open waters. And with the picturesque views that Maine has to offer, I can understand why.

Have you visited Maine’s Central Coast?

Use our app to check medicine names abroad, get embassy info, find security alerts and more!

Note: Available plans and coverages may have changed since this blog was published.


About the Author

Terri Marshall

Terri Marshall, a RoamRight Blog Author

Terri Marshall is a New York City based freelance writer whose work includes travel, spirits, and all things chocolate. Terri's work appears in several publications. She has been a featured guest on Peter Greenberg's Worldwide Travel radio program and Denver's KZKO Radio Morning Express show. Terri will not hesitate to go to the source for great chocolate - even if that means hiking through the jungle and picking cacao pods herself.


Happiest when she's globetrotting, Terri has covered destinations all over the United States, Europe, and into Central and South America. Favorite adventures include reindeer driving in Norway and fishing for piranhas in the Amazon jungle of Peru. You can keep up with Terri's adventures on her website www.TrippingwithTerri.com. You can also find her on Facebook, Twitter and Instagram.

Get A Free Travel Insurance Quote 

Travel smarter with travel insurance from RoamRight. Get your free, no-obligation quote online today.

I'm a partner, take me to my portal

Stay Connected!

Sign up for RoamRight's FREE monthly email newsletter to get travel tips, tricks, news, ideas, and inspiration!

The RoamRight mark is used by Arch Insurance Company and owned by its parent company, Arch Capital Group (U.S.). Insurance coverages are underwritten by Arch Insurance Company, NAIC #11150, under certain policy series, including LTP 2013 and amendments thereto. Certain terms, conditions, restrictions and exclusions apply and coverages may vary in certain states. In the event of any conflict between your policy terms and coverage descriptions on this website, the terms and conditions of your policy shall govern. Click here for privacy notice.

Copyright© 2024 Arch Insurance Company. All rights reserved.