Road Tripping Maine: Our New Favorite Places to Stay, Eat and Fun Things To Do

With visions of coastal walks, lobster rolls, and Wyeth landscapes, my daughter and I set off on a road trip from our home in New York to Maine.  Our tour included three stops: the first just outside of Ogunquit, then on to Portland and ultimately ending our journey in the Rockland/ Camden area. Here are all our latest finds for you to use perfect for extending visiting day weekends, on the college tour, family trips, or for a quick weekend getaway.  

Logistics: An early start from Westchester County got us to the Maine Bridge in time for an early lunch. Skewing our tradition of stopping in Portsmouth for breakfast at The Friendly Toast (though that's always a good idea)  we headed across the bridge to Kittery.  We were excited to try the much-lauded Anju Noodle Bar.  Located in a surprisingly charming section of Kittery,  a two-block stretch with a few cute shops, it was a far cry from the outlet centers that put this area on the map. Anju was delicious, and our new favorite pit stop.  After lunch, windy roads off RT 1 led us to the first stay of our trip, the newly redone Cliff House in Cape Neddick, minutes from Ogunquit and our home for two nights. From there, we spent two nights eating our way around Portland, ending our trip with three nights in Rockland.

Where to Stay: The Cliff House's design-savvy renovations take this 150-year resort hotel to a new level, with stunning views, a soaring lobby and a spectacular oceanfront setting on Bald Head Cliff just ten minutes from Ogunquit's attractions. It's a feel-good kind of place where families sit around the fire pits at dusk making smores. Days lend to taking a walk on the picturesque oceanfront path and rotating between the pool and the hot tub. There are two restaurants, a coffee shop, plus a lovely spa and gym. Though it's a big property, somehow it gets it right. It's beachy and chic, and an excellent addition to Maine's hotel choices. As Cliff House is just over the New Hampshire border, it's a good starting point for a road trip through Maine. On our radar is to try a night or two at The Tides Beach Club located just opposite beautiful Goose Rocks Beach– right outside Kennebunkport. Its a grand looking B and B where sun, sand (beach service is provided) and cocktails on the wide porch make for a perfect day. Nearby their sister property, Hidden Pond is nestled in 60 acres of birch forest. With all different size cottages and bungalows, it's an ideal retreat for families.

In Portland: The Press Hotel has personality and style, and in our opinion is the best place to stay, especially compared to the tired older hotel chains in town. Formally, the offices and printing plant of The Portland Press Herald (Maine's largest newspaper) the hotel pays homage to the building's history with old typewriters in the lobby and newspaper headlines decorating the hallways. The theme continues in the large, comfortable rooms, drawing inspiration from 1920's writer's offices. It's all playful and fun, more whimsy than kitschy and it works. With a key location in the Old Port, nothing is more than a few blocks from the Press.

In Rockland: We checked into the boutique 250 Main just a few years on the scene, overlooking Rockland Harbor on a quiet stretch of the town's Main Street. It's within easy walking distance to the Farnsworth Art Museum and all the best restaurants and shops.  The rooms are simple but stylish, with every room decorated with works by local artists. 250 Main is a welcome alternative for those who want to avoid the more congested and pristine Camden. In my opinion, Rockland is more authentic, arty, and fun. If you wish to stay in Camden, I'd recommend the Camden Harbor Inn, a Relais Chateaux or the more casual Whitehall.

Iconic Eats: You can't visit Maine without having at least one lobster roll, and everyone has their favorite spots. (My all-time favorite, Tubby's, is located in Wayne right down the road from Camp Androscoggin, where my son went to camp for many years.) As my days at Tubby's are long gone, other favorites include: The Clam Shack in Kennebunkport, Eventide in Portland, Bite Into Maine in Scarborough, and Red's Eats in Wiscasset. (You must hit Red's at an off time as otherwise, the line stretches down the block and it's hard to wait an hour for a lobster roll in Maine when there are so many other options.)

Best Bites Ogunquit: We loved our meal at Walkers, right down the road from The Cliff House. We were disappointed with our meal at Barnacle Billy's, a definite miss, though the setting at Perkins Cove is lovely.  We hear good things about That Place in Ogunquit or Northern Union, both on our list for next time.

Best Portland Bites: We always start the day at Tandem Bakery for coffee and biscuits with jam served in an indoor-outdoor converted 1960s gas station. Another morning up early, we ventured to nearby Biddeford to beat the lines at the teeny, tiny, absolutely adorable Palace Diner, housed in a refurbished 1920's train car with only 15 counter seats. We had to have a roman style pizza square for 'blunch' at Belleville after friends raved about it and their amazing croissants as well, a real carb overload. My daughter begged me to go back to Rose Foods, for the second time on our way out of town, for matzo ball soup, latkes, and bagels with all the fixings. We were lucky to land a reservation at Drifters Wife where the food and natural wines live up to all the hype. In the mood for oysters, the Shop at Island Creek or Eventide mentioned above are the places to go. We couldn't decide between Izakaya Minato for Japanese or Cong Tu Bot for Vietnamese, so we decided to try both. After a few delicious small plates at Minato, it was hard to hold back from ordering more, but we were determined to end the night with a pho. We loved both restaurants! We ran out of time but wanted to try Chaval for Spanish influenced fare. Old favorites we didn't hit this trip include Scales, Fore Street, and Central Provisions.

Rockland/Camden Eats: Our meal at Long Grain where the focus is on Asian inspired street dishes was memorable. Go hungry, as you'll want to order everything—just all so good! We always like to eat in the bar area at Primo during a Rockland trip. The downstairs books way in advance, but the more casual second floor is first come first served. If there's a wait, you can have a wander in the garden, wine glass in hand. Primo is one of the original farm to table pioneers and is still going strong after all these years. We ran out of time but would have loved to try Suzuki's Sushi Bar and Nina June nearby in Rockport from acclaimed NY chef Sara Jenkins.

Things to Do: We went blueberry picking at Winslow Farm and outlet shopping in Freeport at L.L. Bean. We spent a few hours at The Farnsworth, a wonderful small museum celebrating Maine's role in American art with an old church devoted exclusively to the works of the Wyeth family. We hung at the beach in Scarborough before walking down the beach to find the cliff path that loops along the ocean ending on the road at the Black Point Inn. (An excellent porch to have a cocktail and watch the sunset) Well worth a detour off 95, located on Route 9 in Kennebunk, is a hidden treasure for garden lovers—Snug Harbor Farm, a magical place where you roam the gardens accompanied by the chickens, ducks, and geese. Even if you can't bring home anything from the nursery, you'll be sure to find something in the lovely garden shop. Snug Harbor is Succulent heaven, and I'm tempted to go on a road trip just to stock up!

For a full Rockland/Camden itinerary, click here.

For a full Portland itinerary, click here


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