Taking a road trip through Maine has been a longtime ambition of mine. My chariot of choice was a new Land Rover Defender 110, and my route would take me and my family up the coast to Rockport Harbor, then north to Old Town for a day of fly fishing for small mouth bass on the Penobscot, then back down for a final night in Kennebunkport—feasting at some of Maine’s best restaurants and soaking up the late summer beauty. I picked up a V8 Defender wearing an earthy, glossy color called Gondwana Stone in Boston. It’s a vehicle I’ve driven off road in a Land Rover Experience, but I’ve never been so free with one as I was in Maine. The balance of heft and power—a 5,700-pound SUV running a 5.0-liter engine with 518 horsepower and 461 pound-feet of torque—all but guaranteed a fun week on the road. It drives like a tank mated with a sports car.
Portland
Inn by the Sea
Our first stop was at Crescent Beach, which is a quick and (mostly) scenic nine-mile drive from Portland. It’s close enough to go into the city for a meal but far enough away to see bright stars and hear only the lap of waves. But you don’t have to go to Portland to dine well, because the inn’s restaurant, Sea Glass, is stellar. Our first meal in Maine was lunch there, and I had the best lobster roll of the trip. Our two-bedroom suite was spacious, with a full kitchen and a large deck overlooking the ocean. There’s a boardwalk leading out to the beach, and the trail is surrounded by bay laurel bushes. At the end of the boardwalk is a station in the woods with towels, cold water and cold beer for the chaise lounges set up for guests. We had rosé by the pool while the kids had ice cream and charcuterie from the poolside snack bar. At night, fires on the lawn were stoked for s’mores under plentiful stars. To a person, everyone I met on staff here left a very warm impression.
The Good Table
A five-minute drive from Inn by the Sea, The Good Table has been a Cape Elizabeth staple since 1986, family run for nearly 40 years before it was sold to its current owners. While I can’t compare the prior version, I was charmed by the restaurant’s current incarnation—the staff, the cuisine, and the excellent cocktails. With dishes like Maine crab cake, local whitefish chowder, cavatelli with Maine lobster, it’s coastal comfort food at its best.
Luke’s Lobster
Luke’s Lobster at the Portland pier is so well located, I was afraid it could be a tourist trap—until I saw how serious their fresh lobster operation is and had dinner here. I felt like a fool for assuming any place with a view this good couldn’t also have incredible food. We sat down next to a bearded Scandinavian man eating two boiled lobsters at a table for one. I had to ask what his story was. He told me he’d just finished hiking the Appalachian Trail from Georgia to Maine, and that this dinner (yes, the one I was currently interrupting) was what he’d dreamed about along the way. With his lobster bib and hands glistening, Luke’s was his reward after 2,197 miles and a couple hundred dehydrated dinners. He had a flight to catch the next morning, and I left him to enjoy his hard-earned gluttony in peace.
From the top-floor windows, we watched a big ship come into port and an old man in a tiny boat who looked like he’d rowed out of an oil painting, while devouring a flight of lobster rolls. After dinner, Luke’s Assistant GM Brian Noble gave us a tour of their lobster operation. They have a dock on the property where lobster boats can unload their catch. Once inside, they’re kept in circulating and temperature controlled water that mimics the ocean for never longer than a day or two before they’re sold to points around the globe. Noble explained to us that bigger is not better with lobster, and there is an optimal size for flavor and tenderness—turns out “average” is actually ideal.
Maine & Loire
That patio at Inn by the Sea was begging for a bottle of good wine, and for that we went to this serious modern wine shop in Portland. We bought a mixed case that served us well on our journey north where high-end wine shops were scarcer.
The Clam Bar
An elevated version of an outdoor seafood shack on the river in Portland’s West End, in an area surrounded by dry docks and shipyards. Ironically, I got the burger, and I didn’t regret it. My family went the seafood route, and I can vouch that it’s great, too. Cocktails are better than you’d ever expect from a seafood shack, with standouts like the vaguely Tiki-adjacent Howler Monkey, which is vodka-based and tropical with hints of coffee and chocolate, and an also Tiki-esque Pain Killer with an optional dark rum floater that will make you want to order another burger.
Heading North From Portland
Maine Fly Company
With as many cool outdoor products that are made in Maine—and considering that fishing is one of the things the state is known for—it came as a shock to me that until recently, there was no made-in-Maine fly rod. An avid angler named Jeff Davis decided to change that in 2018, when he left a corporate C-suite to launch a brand of fly rods inspired by his father’s love of fishing and Maine’s fly fishing legacy. Davis gave me a tour of his fly shop and the space where he and a handful of craftspeople make their rods, and he loaned me his personal rod to take with me to the Penobscot. The shop is in an historic brick building in Yarmouth on the edge of Royal River. The rods are named for different bodies of water around the state: The Kennebec, The Carrabassett, The Moose River, and others. It’s open to the public, so for any and all lovers of fly fishing (or even just the fly-curious) this is a mandatory stop 20 minutes north of Portland.
Rockport Harbor
Rockport Harbor Hotel
If you close your eyes and dream of how pretty a Maine harbor could be, that’s what you get when you come around the bend in the windy coast road and catch your first glimpse of Rockport Harbor. For the visitor, there’s no better way to perch yourself at the center of this view than to stay at the Rockport Harbor Hotel, located on a hill just above the waterfront. With a lobby restaurant, a penthouse restaurant and bar, and a destination restaurant next door, you could stay here for days without having to leave the premises and still eat well. A steakhouse and oyster bar, 18 Central, is next door to the Rockport Harbor Hotel, and locals in the area—like my old Los Angeles friend and groomsman Dave who joined us—view it as one of the best restaurants in this part of the state. The hotel is just an 8-minute drive from the town of Camden, which is as much of a platonic ideal of a Maine village as Rockport Harbor is of a Maine harbor.
Rayr Wine Shop
Because the wine we bought in Portland didn’t go as far as we’d hoped, it was a bit of luck to stumble into this excellent Rockport Harbor wine shop in an ivy-covered mansion on the outskirts of town. (Beware that the staff will likely talk you into a nicer bottle than the one you walked in for, but you’ll thank them later.)
Old Town
Old Town Canoe Factory
I’ve been paddling Old Town canoes since I was a kid at summer camp in 1980s North Carolina. So, the name Old Town has a certain resonance within my memories before I even got to the town it’s named for. The new Old Town Canoe facility is shared with sister brands such as Hummingbird and Jetboil, and the factory floor, where Old Town canoes and kayaks are made, is a thing to behold—think Willy Wonka does watercraft. Barrels of colored plastic beads and giant steel molds where the plastic is heated into ship shape, so to speak. Johnson Outdoors’ Marketing Director Ryan Lilly—and my fly fishing partner for the day—showed me a large, ancient wooden filing cabinet filled with cards for every old wooden canoe they’ve sold, stretching back a hundred years.
I had never been fly fishing from a kayak before, and the idea intimidated me. Turns out my definition of “kayak” needed an update. What Lilly trailered to the Penobscot was a pair or Old Town Autopilot kayaks, which not only eliminate the need to paddle, but have a GPS anchor system that will lock you in place so you can ignore everything but your casting. Traversing the lake with a quiet electric motor doesn’t interrupt the vibe or scare the fish, and I caught several small mouth bass on the Maine Fly Rod, and the fight they put up is a lot of fun.
Waterville
Lockwood Hotel
Unlike the coast of Maine, which is clustered with cute inns, the inland areas of the state are another story. Heading south from Bangor via the inland route is stunningly beautiful in terms of nature, but you have to choose your overnight accommodations wisely. The Lockwood Hotel is part of Charlestowne Hotels, which I know because it’s based in my hometown of Charleston, so I knew any property of theirs would be a good bet. The hotel’s restaurant, Front & Maine, is the kind of place where you’d get your visiting parents to bring you if you were a student at nearby Colby College. Both the cuisine and the cocktails were top notch, and the service was chummy but also precise. Our room had a view of the Kennebec River, which is as wide and dramatic here as the Mississippi.
Kennebunkport
For our final night in Maine, we wanted something special, and Hidden Pond has special to spare. A luxury resort made up of cabins and houses in the woods near Kennebunkport, just checking in made us regret that we only had one night to spend there. Our cottage in the woods had a large and fully stocked kitchen, and a screen porch for polishing off our last bottle of wine later that night. We had lunch poolside under a canopy of trees by the main lobby building, then the kids got into tie-dying shirts in a vegetable garden shed. We managed to get a coveted reservation at Earth at Hidden Pond, which is open to the public and very hard to get into. Dinner at Earth was superb, with smothering service, garden-garnished cocktails, and a farm-to-table menu rivaling any Northern California haute cuisine. But book ahead, book very ahead. We only spent one night at Hidden Pond, but many months later my kids still ask to go back—and ask for it by name.