Two Nights in Wiscasset, Freeport, Westbrook, and Portland, Maine

Finally, some sun in the middle of the rainiest summer ever! We celebrated with a two-night stay in Freeport, Maine that included lots of sightseeing along the way.

Wiscasset, Maine: Red’s Eats and “the Marie Antoinette House”

From Mariaville on a Thursday morning, we drove two hours south to Wiscasset, Maine, lovingly called “the prettiest village in Maine.” We arrived around eleven a.m., just in time to join the line growing outside Red’s Eats. Red’s Eats is a small food stand that specializes in lobster rolls—they have multiple times won best “best lobster roll in Maine” and even “best lobster roll in New England”—and has been featured on several food and travel shows. The stand opened at 11:30 a.m., and we were just far enough back in line to be ordering right at noon, meaning we stood in line for an hour total. The friendly staff were kind enough to bring our pup a water bowl and even a whole cold hotdog for free, which she gobbled up happily. Brandon’s assessment was “you get your money’s worth of lobster,” which is good since with market-rate pricing you can expect to shell out (get it?) $34/roll [as of June 2023].

Wiscasset is for sure a pretty village, with some of the grandest and best-kept old manors on its flower-lined streets. Head west to find Tucker Castle, which you can tour, or simply step around the back of the castle for an unobstructed view of Cod Cove as well as “the Marie Antoinette house” across the Sheepscot River in neighboring Edgecomb, ME. (Legend has it the house was being prepared as an escape house for the French queen, but she was executed before Captain Samuel Clough could bust her out of the Bastille.)

Freeport, Maine: L.L. Bean and the Maine Desert

From Wiscasset, we tooled another forty-five minutes down Highway 1 to Freeport, Maine, which I dare say rivals any town in Colorado for most devout commitment to outdoor living. In addition to an enormous L.L. Bean campus, with four separate giant buildings variously dedicated to hunting/fishing, retail, home, and ski/boat—and organized around a green space with a concert venue—there are outlet stores for Patagonia, Orvis, the North Face, and Toad&Co, too. After we shopped, we dropped—right into the patio chairs outside Ben & Jerry’s for some sorbet.

Thursday night, we checked into the Desert of Maine campground, so-called because it sits on Maine’s only “desert.” For real: There are twenty square miles of sand dunes surrounded by forest. The set-up was a great comparison site for what the Lincoln School will be someday, with simple cabins served by a central bathhouse. Our A-frame-style cabin had a fire pit, party lights, and picnic table outside, while inside, one whole wall was a window—perfect for forest-bathing away from the bugs.

Maine Beer Company

Maine Beer Company, Freeport

Bonus: All of Freeport’s shops, as well as the campground, were dog-friendly. So was pizza at the nearby Maine Beer Company.

Westbrook, Maine: REI and Chase Bank

Given that Maine is the home of L.L. Bean, it makes sense that the REIs (an outfitter chain that calls Seattle home) would be few and far between. There’s one in Westbrook, Maine, though, and as REI was having their Fourth of July clearance sale this weekend, Friday morning we headed that way. It just so happens that REI shares a parking lot with Chase Bank … significant only if you’re a Chase Bank client and looking for a free ATM withdrawal (which we were). There are no Chase Banks north of Falmouth, ME.

Portland, Maine: El Rayo Taqueria, Shopping, and Maine Potato Donuts

Friday afternoon we spent bumming around Portland, the largest city in Maine and a bustling tourist hub. Commercial Street hugs the coast and is lined on both sides with shops and restaurants. It definitely seemed to be the most-packed street. We liked Fish & Bone’s amazing array of pet supplies and all the cute Maine-centric kitsch spilling out of Commercial Street’s shops. For lunch, we took the dog to the dog-friendly patio at El Rayo Taqueria (think huge rice-and-bean bowls with your choice of proteins), but went back to Commercial afterward for a box of Holy Donuts. (In Brandon’s words: potato donuts are “chewier, moister, and all-around better” than regular donuts). I preferred the gluten-free and vegan cupcakes at B+B Bakery!

My favorite street was Exchange Street. Still firmly in the Old Port District but set slightly back from crazy Commercial Street, there were some more tasteful locally owned shops and architecture to make your jaw drop.

We stayed a second night at the Desert of Maine campground so we could enjoy another campfire (they sell wood, kindling, and matches on the honor system at a kiosk) and also check out the sand dunes. After the desert closes to the public, guests of the campground can still access the dunes, where dogs can frolic off-leash as the summer sun sets.

An amazing two nights downeast!

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Five Things to Do in Ellsworth, Maine

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Visiting the Green Lake National Fish Hatchery