200 miles south of the Canadian border the idyllic town of Portland, Maine rests on a rugged Atlantic peninsula jutting out over Casco Bay. Six lighthouses welcome visitors to the city’s rocky shoreline — a rich bricolage of history, art, culture and incredible dining.
After a wedding in Brooklyn earlier this summer we spent a weekend adventuring around Portland and beyond before heading on to Acadia National Park.
Located near the southern end of Maine’s rocky coastline, it’s easy to reach Portland by car and plane and, from many cities, by train. We opted for the latter option and kicked off the trip with a stress-free, sustainable Amtrak Northeast Regional ride from Penn Station to Boston. After a short layover in North End over a big plate of Spaghetti Puttanesca we boarded a connecting Amtrak Downeaster on into Portland, arriving a couple miles from downtown just before sunset.
We rented a car to get out to our incredibly serene, wonderfully appointed Airbnb on Cape Elizabeth but could have likely used Lyft and a couple of bicycles to get around had we stayed closer to Old Port — Portland is a very walkable city with a robust public bus network and plenty to do near city center.
After unpacking and unwinding, the next morning kicked off a full weekend of sights and bites:
Start the day with one of Maine’s most beloved bagels at Scratch Baking Company. For more than a decade Scratch has served breakfast faire on Willard Square — pastries, breads, light eats, and tasty sweets. Fill up your thermos with hot coffee and grab a snickerdoodle to go before heading on to see each of Portland’s lighthouses.
From Scratch, carve out around four hours and take this lighthouse tour in reverse. Have a quick look at little Bug Light and cruise over to nearby Spring Point Ledge Light, then spend a couple of hours enjoying the trails that wrap around the incredible Portland Head Light at Fort Williams Park (with Ram Island Light in the distance) before ending with a scenic drive to Two Lights State Park.
If you’re without a car, for $26 you can see everything but Two Lights via boat aboard a narrated Portland Discovery tour. Both the company’s trolley and boat tours conveniently start and end on Commercial Street in downtown.
Should you find yourself at Portland Head Light between lunch and early dinner hours, be sure to grab a Moxie soda and perfect lobster roll at Bite Into Maine, a little food truck that delivers big on taste with everything from hot-buttered Connecticut style rolls to wasabi and curry mayo options.
Finish out the afternoon with some quiet time along the shore at Two Lights State Park (on the way there, stop by C-Salt for blueberry tea bread or Alewive’s Brook Farm for fresh vegetables to snack on).
Kick off the morning with breakfast from Standard Baking Co., another longstanding Portland staple for scrumptious pastries and breads.
From Standard, cross the street to Casco Bay Lines Ferry Terminal and book a ferry to explore one of the surrounding islands for a couple of hours:
- Quirky Peaks Island is the Lines’ most popular option for visitors — a 20 minute ferry ride takes you to the small island known in the late 1800s as the Coney Island of Maine that later became a World War II outpost. Today Peaks Island is home to a few restaurants, coffee shops, and art galleries, as well as the 5th Maine Museum and ever-so-quaint Umbrella Cover Museum. Rent bikes (they’re on the honor system most of the year), take a kayak tour, or opt for a guided golf cart tour. Peter Anderson, a Peaks Island local, gave us a charming tour around the entire island complete with historical highlights and the stories behind his favorite houses — you’ll find him holding a tour sign just after stepping off the ferry.
- A bit farther out, quieter Diamond Cove on Great Diamond Island has a general store and upscale restaurant, historic Fort McKinley Museum, and the occasional yoga class. There are a few beaches, parks, and roads along the island, but you’ll need to stay at The Inn at Diamond Cove or know a resident in order to access them — the majority of the island is a gated community.
- Beyond Great Diamond lie Long Island, Chebeague Island, and Bailey Island, each of which offer at least one restaurant, market, and inn, along with activities for visitors in the warmer months. There’s also shy little Cliff Island, a rural H-shaped summer getaway with dirt roads and a one-room schoolhouse.
Either before or after your island hop, drop into Edgecomb Potters and have a look at their beautiful zinc-glazed mugs and dishes, or pop by the back deck at Liquid Riot for a beer or spirits tasting and small bites.
Consider taking the one-mile stroll along cobbled streets up to Encore Vintage, a spacious fashion outpost with a rambunctious owner whose collection includes everything from Chanel tweed suits and Ferragamos to Pucci skirts and traditional Japanese wedding kimonos.
At some point during your stay, it’s also well worth the 5 mile drive inland to visit Allagash Brewery (and perhaps their next door neighbors, Spare Time and Foundation Brewing). Allagash offers free tours and tastings 11a-6p daily and you can buy most of their beer to go, including a few brews available only on-site. Our favorite was James Bean, a bourbon barrel-aged Belgian infused with cold-brewed coffee. If you’d like to go on the free tour, be sure to book online a day or two in advance. Otherwise, you can just drop by without a reservation for a free tasting.
On your way back from Allagash drop by Bissell Brothers Brewing, another favorite local brewery that’s open a bit later in the summer. You can also hop on The Maine Brew Bus for Beerunch or a Best of Portland tour that visits a number of local breweries.
Finish your weekend with an exceptional dinner at Eventide Oyster Co., where the menu changes daily but there’s always a brown butter lobster roll, fresh oyster or two, and tiki-touched beverage waiting for you. Eventide only accepts reservations for parties of six of more, but plenty of indoor seats paired with a patio means the wait is never much longer than the time it takes to savor a Mai Tai while soaking up a few songs from their summer playlist.
What I’m wearing:
- Tradlands ‘The Arapahoe’ Flannel Buttondown
- Filson Cover Cloth Mile Marker Trench and hood
- Patagonia Down Sweater Vest
- Vintage silk scarf (similar)
- Ray-Ban Original 58mm Polarized Aviator Sunglasses in gold
- Beyond Yoga Take Me Higher Long Legging
- Allbirds Women’s Wool Runners
- Wigwam ‘Countryside’ Socks
- Tense Small Leather Hampton Watch in dark sandalwood and olive ℅ This watch is made of reclaimed African sandalwood and Italian leather with a Miyota Japanese movements and Mother of Pearl dial. Like every watch the company has created since 1971, it’s built by hand in Tense’s Vancouver, BC workshop. Bonus: The lack of cold steel makes wearing it through airport security a breeze.
Size, fit, shopping standards, and everything else that’s in my closet right here.
Also on this trip: A complete travel guide to Acadia National Park.