Rockland rocks. Named a Distinctive Destination by the National Trust for Historic Preservation, the small Maine coastal city edging Penobscot Bay retains the heart and spirit of a working town, buzzes with the added pizazz of excellent museums, a vigorous arts scene, surprising restaurants, eclectic shops, and delivers a more than generous serving of lobster, lighthouses, and windjammers.
Plunk down in Rockland, for a few days, and you’ll experience the best Maine has to offer—without having to put endless miles on your vehicle. Heck, thanks to air, bus, and train service and a compact downtown, you can even get by without a car (and in 2012, when the Amtrak Downeaster connects Boston to Brunswick, via Portland, it’ll be an easy transfer to the Maine Eastern Railroad excursion train to Rockland).
Why do I love Rockland? For so many reasons, I had to be a bit creative when naming my top 10.
Lighthouses, camera, action
Begin at the Maine Lighthouse Museum, after soaking up the facts, legends, and lore, put on your walking shoes for the nearly one mile jaunt over the jetty to Rockland Breakwater Lighthouse at the tip (usually open on weekends, when volunteers are available). Next hop in the car and mosey over to the Owls Head Light, then segue over to the St. George Peninsula to Marshall Point Light.
Lobster!
Oh, yes, Rockland, home of the Maine Lobster Festival, has you covered, with some form of the tasty crustacean on nearly every menu in town. Prefer to roll-up-your-sleeves and muckle on to one and have at it on an oceanfront picnic table? Yup, got that, too.
Two faves: Waterman’s Beach Lobster, in South Thomaston, and Miller’s, in Spruce Head, both within 15 minutes of downtown Rockland. And if you want to know the nitty-gritty about the tasty crustaceans, join Capt. Steve Hale aboard the Captain Jack, a 30-foot working lobster boat for a 1.25-hour hauling cruise.
Arts
It wouldn’t be a stretch to call Rockland Maine’s most art-centric town, thanks to the fabulous Farnsworth Museum and the galaxy of independent galleries that surround it. Take it all in on the monthy First Friday Art Walk, or get a sampling of local artists and artisans at the Saturday Art Festival in Harbor Park. Catch a concert, lecture, performance, or film at the Strand, a beautifully restored 1923 theater downtown.
Shop
Independent shops, thrift stores, boutiques, and galleries line Rockland’s Main Street, from Planet Toy (let’s play!) on the south end to Fiore (extra virgin olive oils, mmm!) on the northern end, and branch out from there. In between, find clothing, kitchenware, island-made arts, museum shops, a bookstore, pet boutique, and so much more.
Puffins
C’mon, you know you’ve always wanted to see those funny looking birds, those clowns of the sea. If you can’t manage a trip to see the puffins, the Project Puffin Visitor Center will bring them to you. Watch live videos of nesting puffins, explore interactive exhibits, and view films highlighting the successful efforts to restore and protect them. On Wednesdays evenings during July and August, there’s a weekly lecture series. And you can find out about seasonal puffin-viewing trips.
Trains, planes, cars, and boats
For transportation buffs, the choices are plentiful. The Owls Head Transportation Museum, just over the town line in Owls Head, is a must. Everything on view—wheels and wings—is in primo condition, and on special event weekends throughout the summer, the planes soar, the bikes role, and the cars motor by. Newer on the scene is the waterfront Sail Power & Steam Museum, where displays highlight Rockland’s maritime heritage. And the Maine Eastern Railway is an excursion train connecting Rockland with Wiscasset, Bath, and Brunswick.
Windjamming
Rockland views with Camden for the title of Maine’s windjammer capital. About half of the Maine Windjammer Association fleet is now based here. If you can’t get away for a few days, book a two-hour sail aboard A Morning in Maine, Capt. Bob Pratt’s 55-foot ketch, designed by noted naval architect R.D. Culler and built by Concordia Yachts. Best vantage points for viewing and photographing windjammers sailing in and around Rockland Harbor are the Rockland Breakwater and Owls Head Light (Hint: Best photo opp is during the annual Maine Windjammer Association Parade of Sail event in July).
Eat!
Portland may get all the attention, but Rockland’s food scene is no slouch. Start with two James Beard award winners: Melissa Kelly, who owns Primo, a farm to table restaurant on the southern edge of town, with her partner Price Kushner (be sure to tour the gardens and animal pens before dining in the restaurant or upstairs lounges), and Waterman’s Beach Lobster, named an American Classic. Stroll down Main Street, and the possibilities include the region’s best French, Lily Bistro; best Japanese, Suzuki’s Sushi Bar; best wine & tapas, In Good Company. Craving Mex? Tuck into Sunfire Mexican Grill or head to the harbor for take out at Shell’s Southwest Grill. For eclectic ethnic overload, Cafe Miranda rules. Indulge in breakfast at The Brown Bag or Brass Compass. Head to Sweets & Meats Market for fabulous sandwiches. And if you’re in for an adventure, wander into Conte’s. And those are just off the top of my head.
Sip
Sure you can drive yourself, but why not let All Aboard Trolley doing the driving while you do the sippin’ on its Nap-ah Valley Wine Tour, with stops at three area wineries: Sweetgrass, Savage Oakes, and Cellardoor. Explore two other local members of the Maine Wine Trail on your own Breakwater and Oyster River.
Island hop
Ferries tether Vinalhaven, North Haven, and distant Matinicus to Rockland. Both Vinalhaven and North Haven are great day trips. Ferries are also the least expensive way to see the coast from the water. Don’t even consider bringing a car to either, unless you’re planning a long stay and need it to get around (you can rent one on Vinalhaven); foot or bike are the preferred methods of getting around on both. The ferry to Monhegan departs from Port Clyde, about a half-hour’s drive south from Rockland, and well worth a day trip.
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Where to stay:
Best bets intown are the four member inns of the Historic Inns of Rockland: Berry Manor Inn, Capt. Lindsey House, Granite Inn, and Limerock Inn. Each is in the city’s historic district and within walking distance to all downtown sights. The Samoset Resort, within walking distance of the Rockland Breakwater, is a full-service oceanfront property with golf course, spa, and all the other whistles and bells you’d expect.









Southern Coast
Greater Portland
Mid-Coast
Penobscot Bay
Blue Hill Peninsula
Acadia Region
Down East
Aroostook County
Maine Highlands
Kennebec Corridor
Western Lakes & Mountains
What about Bricks Restaurant?? We were in Rockland last summer and the pizza was AWESOME! It became our favorite place to eat. They also had a $5 lunch deal that included our drink! Great view and service. I’d like to see it included in more of these articles!!!
Excellent top 10 Hilary, really spot on! Any chance this gets picked up by a bigger outlet like the Boston Globe (like many of your other articles)?
My only addition to this list would be the best breakfast spot and one of the best lunch spots in town – Home Kitchen Cafe.