About a year ago, Austin got an idea in his head that we absolutely had to attend the Maine Lobster Festival. I didn’t initially meet this suggestion with great enthusiasm. Maine? When we could visit… somewhere else?
The more I researched Maine, though, the more I wanted to visit, so I told Austin I was on board. We ended up building out a four-day weekend in August 2014 to coincide with the annual Lobster Festival.
We opted to fly into Boston, versus directly into Portland (about a 100 mile drive north) because tickets were significantly cheaper, and it would let us catch up with some friends on our way out of the city. We took an easy Porter flight from Toronto City Airport (YTZ) into Logan International (BOS) on Friday morning, meeting a college friend, Eliza, and her boyfriend Phil, who flew in from DC for the weekend. We picked up our car rental, and were on our way.
An aside, on booking a rental car: We initially booked a car in downtown Boston, planning to take a cab from the airport, because the airport was quoting us almost $700 (!) for a four-day rental. A day before we departed, Austin rechecked the rates and found an airport rental for about half the originally quoted price. Because rental companies have lenient cancellation policies (up to 24 hours before the scheduled rental) he cancelled our Boston car and booked the airport rental.
A few weeks before flying out, I stumbled upon a piece about the best baked goods in America, which raved about Boston’s Flour Bakery sticky bun. We weaved through some serious mid-day Boston traffic to hunt one down. I’m happy to say it delivered… after a 15-minute wait, a new pan came out of the oven and we each dove into a caramel and pecan puddle covering tender and sticky dough. Lunch of champions.
After a drive along Highway 1 (I would regale you with the scenery, but I am an expert at falling asleep the minute I get into a car) we made it to Portland. We parted ways with Eliza and Phil, whom we would rejoin later that weekend in Rockland for the Lobster Festival.
We checked into the Portland Harbor Hotel, where Austin had booked us a charming room for the night. It was a perfectly nice hotel — well-appointed historical accommodations with traditional rooms. Upon return to Portland, we’d probably opt to stay at an Airbnb, but given our short stay, it worked well.
An aside (and word of caution), on parking: Portland Harbor Hotel has a seriously sketchy parking setup. You’re led via clearly marked signs to “Hotel Parking” and only once inside the underground garage, do you realize it’s valet-mandatory $18-a-day parking. Not cool. We learned chatting with other guests that we were not the first people caught by this practice. Save yourself with inexpensive street parking, or park in the garage next door.
We quickly dressed for dinner reservations at Hugo’s, a restaurant that came highly recommended in our research on Portland. The restaurant was a short walk from our hotel — about 10 minutes — so we set out on foot in the stunning Portland dusk, lamenting that we only had a day to explore the city before continuing our travels.
We settled in their lounge as we waited for our table to be prepared. Flipping through the small but smart wine list, we were impressed by the quality of selection and reasonable price points (such a shocking difference from Toronto’s overpriced wine lists!). We agreed on a stunning little 2007 Blanc de Noirs from Schramsberg in Napa Valley.
An aside, on branding: Hugo’s branding was spot-on — the menus packaged in beautiful dusty teal linen hardcovers, printed on luxurious cream paper and using just the right typefaces to convey their brand. My paper nerd was impressed.
A glass of wine in, we were led to our kitchen bar seats in front of the garde manger. Eating at kitchen tables is one of my favourite ways to enjoy a tasting menu — I love being able to interact with the chefs, watch the food go out and see the course progressions for each table.
Hugo’s offers three set five-course tasting menus — Foraged & Farmed (meat), From the Sea (seafood), and Forest & Field (vegetable). We opted for the meat and fish menus, sticking with our usual approach of swapping dishes half-way through each course.
The meal was sublime. Austin noted, and I agree, that it stood up to $1000 tasting menu tabs — and he’d rather have this meal again three times over. I will make note of one spectacular dish from the Foraged & Farmed menu: my best restaurant dish of 2014. As someone who has enjoyed a lot of fine dining that tends toward modernist, it’s rare I am served a dish so completely unexpected that I’m not sure what to make of it. This happened at Hugo’s. I even emailed the restaurant after we returned to Toronto to ask about it; it so strongly stuck with me. Here’s the reply I received from Owner and Executive Chef, Mike Wiley:
RE: That Pushed Egg
What a fine compliment it was receiving your email! Not only to learn that you enjoyed the dish, but that it resonated to the point that you needed to get in touch with us–all of it is quite flattering.
So, the dish then: it was a hard-boiled egg pushed through a potato ricer. We dressed the egg with a nasturtium vinaigrette, and garnished the egg with a changing array of fresh and crunchy elements, including but not limited to, grilled breadcrumb, bacon crumble, tomato water gelée, dehydrated prosciutto crisps, dehydrated black olive, radish micro greens, thinly sliced radish, and pickled shimeji mushroom. The thinking behind the dish was that eggs are delicious and the vinaigrette was tasty, so those baseline elements could support a whole host of crunchy, salty, and sour garnishes.
Thanks again for your kind email, we look forward to cooking for you again.
Hugo’s was a meal to remember and an occasion of its own to return to Portland. Sated and exhausted from a long day of travel, we walked back to the hotel and fell into a deep sleep.
We hopped out of bed early (Austin and I can never sleep too late on vacation) with donuts on the mind. The Holy Donut
, specifically, a revered donut shop in downtown Portland. They specialize in Maine potato-based donuts, which are tender, fluffy and decadent. As is often the case, we ordered way more than we could eat — one each of the Fresh Lemon (my favourite), Chocolate Sea Salt (Austin’s favourite), Coconut, Allen’s Apple Brandy, Sweet Potato Ginger and Old Fashioned. As a last minute “what the heck!” we also ordered a savoury filled bacon cheddar donut, which was the best of the bunch.
Full of donut, we checked out of the hotel and made our way to the open-air Portland Farmer’s Market
, held every Saturday morning from March through December.
What a market this was! I’m a bit of a market hound — I like them open and covered and seasonal and year-round and this was a very good example of an outdoor version, focused on heirloom and organic produce. We ogled the veg and picked up a wildflower bouquet for our hosts in Waldoboro, who we would see later that evening.
We made our way to South Portland to begin an afternoon of lighthouse exploring. Our first stop was the grounds of the abandoned Goddard Mansion
in Fort Williams Park, where we meandered through the woods and along the shoreline taking in the salty, overcast day.
We drove a short distance to our first lighthouse, the famous Portland Head Light.
This lighthouse is not open for climbing or tours, so we quickly made our way around its periphery before making a bee line to the main attraction — our first lobster roll of the weekend!
An aside, on butter versus mayonnaise:
Maine prepares its lobster roll with a mayonnaise dressing. Through and through, I am Connecticut-style — naked and drowning in butter has my heart. Thankfully, we didn’t get too many odd looks for ordering most of our rolls without mayo over the weekend.
Happily refueled, we headed to our next lighthouse and favourite of the weekend, Spring Point Ledge
. One of the most memorable parts of our trip was skipping along the breakwater to this lighthouse, reaching for Austin’s hand, and squealing in fear as I tried not to fall into the massive crevasses between the boulders.
We climbed the three levels to the top of the lighthouse, guided by some sweet old Maine residents who regaled us with the site’s past and explained the logistics of its sleeping quarters and maintenance. We enjoyed a moment of solitude at the apex, looking out at the ocean and taking in the postcard-like views of the overcast day.
Full of lighthouses (for now) we returned to downtown Portland for some more eating and exploring before heading north. While I could have spent several days exploring Portland’s artisan and craftsman shops, a few standouts were Portland Dry Goods
(I could build Austin and my wardrobes solely from that shop), Cabot Cheese’s Farmers’ Annex
(delicious cheddars) and Chellis Wilson
We wandered through the harbour to J’s Oyster
, a hole-in-the-wall seafood bar that came recommended over and again as the place locals went for their oyster fix. It was nothing fancy and totally hit the spot — a dozen just-caught briny oysters with a pint of Allagash
washing everything down. We poked around some more shops along Fore Street as we made our way to Eventide Oyster Co.
— Hugo’s sister restaurant — for their lauded lobster roll. It was swimming in a brown butter vinaigrette and piled high into a soft, steamed-style bun.
Knowing we had a couple hours of driving before us, we set north toward Waldoboro, where we were staying the next two nights. After saying hello to our hosts and enjoying a drink, we dressed for dinner with Eliza and Phil at Primo
Oh, Primo! Leading up to our trip, I had done some research about the restaurant and its Executive Chef, Melissa Kelly. With an impressive resume (two James Beard awards, stages at restaurants like Chez Panisse) she opened Primo in 2000 in her native Maine on a 4.5 acre farm that supplies about 80 per cent of the restaurant’s raw ingredients. With such an idyllic story, it was hard to imagine we wouldn’t love Primo, but it went beyond our expectations. The farmhouse restaurant was cozy and refined, the service warm and flawless and the food tasting of farm and ocean. We hear the term farm-to-table used so often (and carelessly) these days that it loses meaning, but Kelly’s restaurant was platonic form.
We woke early for the drive to Rockland for the “maine” (sorry, couldn’t resist) event — the Lobster Festival
. Eliza gave us fair heeding about this touristic phenomenon, but the kitsch was every bit wonderful. We ate giant lobster dinners, watched milk crate races, took some cheesy photos and ate more lobster. Was it the star attraction of the weekend? Hardly. But I’m so glad it’s what brought us to Maine in the first place.
Bellies full, we were back on the road early-afternoon to seek out our final lighthouse of the weekend, the charming Owl’s Head Light
. We arrived just as they were wrapping up tours for the day, and made our way to the top for some spectacular views of the Maine coastline.
Back into Waldoboro, we stopped off at Eliza’s high school digs, Captain’s Fresh Idea
, for — what else — more lobster, plus some strangely delicious deep fried string beans. We tucked a whoopie pie (Maine’s official dessert) into my purse to enjoy later, and made our way home for a bonafide Maine lobster dinner, complete with cheeky aprons.
Our final day in Maine began with breakfast at Moody’s
, an iconic American diner established in 1927. While most of us opted for a traditional American breakfast, we spent the meal staring wistfully at Eliza’s mom’s fresh strawberry pie.
Back on the road, we drove about an hour south along Highway 1 through the town of Wiscasset, fondly known as the prettiest village in Maine. We strongly considered stopping off at Red’s Eats
, one of the state’s most iconic lobster shacks, whose line was snaked around the block even given the hour! Alas, it was a bit too early for lobster, so we continued south.
Our next stop was Freeport, to visit the L.L. Bean Flagship Store
and its infamous boot sculpture. While L.L. Bean is a reach from my usual aesthetic, I was happy to see how the hunter-type live and pick up a cozy sweatshirt to bring home.
Over the course of the weekend, we debated breweries to visit, knowing we only had so much time with so many respected craft brewers along the coast — Allagash, Smuttynose, Oxbow,
to name a few. Ultimately, we ended up at Shipyard Brewing Co.
‘s Portland headquarters, where we sampled their lineup of brews with a hilarious and knowledgeable taster from Montreal. Our standout beer was the Double ESB, a bourbon barrel aged ale.
With one meal left in Portland, it was a serious debate over lunch at Duckfat
versus Miyake Sushi
. Duckfat is a local icon with an indulgent bistro menu. Miyake is consistently named one of the best sushi restaurants in America
. Our group was divided. Ultimately, the wait at Duckfat led us to Miyake, where we were able to snag four seats at the chef’s bar. I immediately knew what I was ordering — the Daily Bento Box, which defied every preconception I have about bento boxes. This was a little jewel case of art: yuzu-steamed clams, perfect sashimi with fresh grated wasabi, delicate grilled and glazed eel and miso braised vegetables in earthenware.
Barely any room in our stomachs, we walked along Fore Street for a final Portland stop at Gelato Fiasco
— home to some of the tastiest and best branded gelato in the States. Our charming server, Kristina
, was happy to help us taste through the flavours and made Austin a delicious pour-over coffee. My dark chocolate sorbetto paired with their signature sweet resurgam gelato in a house-made waffle cone was out of this world.
It was time to drive to Boston for our flight home.
We met up with Austin’s old college friend (and our beloved wedding Master of Ceremonies!) Tarik and his girlfriend (now fiance!) Pat at El Pelon
— Boston’s celebrated taqueria — for a bite before our flight departed. While I was sated from a day spent stuffing myself silly, I did enjoy a strawberry agua fresca and a taste of Austin’s top-notch El Guapo burrito heaped with grilled steak and fried plantains.
Maine was a perfect extra-long-weekend trip for a group of food lovers who also love the outdoors and ocean air. Austin and I agree that when we return it will be for a week, with Portland as our home base and a rental car for day trips up and down the coast. One thing’s certain: we still have left enough restaurants to eat at, lighthouses to visit, breweries to explore and lobster shacks to cross off our list!
Planning Your Trip
Shop & Stay
Portland Harbor Hotel, Portland, ME
Portland Farmer’s Market, Portland, ME
Portland Dry Goods, Portland, ME
Chellis Wilson, Portland, ME
L.L. Bean Flagship Store, Freeport, ME
Flour Bakery, Boston, MA
Hugo’s Restaurant, Portland, ME
The Holy Donut, Portland, ME
Bite Into Maine, South Portland, ME
Cabot Cheese’s Farmers’ Annex, Portland, ME
J’s Oyster, Portland, ME
Eventide Oyster Co., Portland , ME
Primo, Rockland, ME
Captain’s Fresh Idea, Waldoboro, ME
Moody’s Diner, Waldoboro, ME
Red’s Eats, Wiscasset, ME
Duckfat, Portland, ME
Miyake Sushi, Portland, ME
Gelato Fiasco, Portland, ME
El Pelon, Boston, MA
Goddard Mansion and Fort Williams Park, Portland, ME
Portland Head Light, Portland, ME
Spring Point Ledge Lighthouse, South Portland, ME
Maine Lobster Festival, Rockland, ME
Owl’s Head Light, Rockland, ME
Shipyard Brewing Co., Portland, ME
5 Things: Portland, ME on Hither & Thither
The “Maine” Tag on Map & Menu (Meredith and Michael live in Maine and were a huge resource as we researched our trip!)
The 10 Best Lobster Shacks in Maine on Travel + Leisure
36 Hours in Midcoast Maine on the New York Times Travel
The Restaurant Guide to Portland, Maine on Conde Nast Traveler
[Our complete Portland, Maine photo set on Flickr]