My friends and I have taken an annual trip to Portland, Maine, for the past three years. The primary focus of this trip: breweries. Although there is a ton to do in the city besides craft beer, this brewery road trip has become our spring tradition. I’ve synthesized the highlights of our trips for this recommendation for a roughly 26-hour guys’ weekend in Portland (plus a few more suggestions if you want to extend it for the afternoon). Although our trip is typically in the spring, this trip can be taken any time of the year.
Our Itinerary
Leaving the South Shore of Massachusetts around 9:30, the first destination time and again is Bissell Brothers Brewing. Bissell Brothers is located at Thompson’s Point, at the edge of the city, and easily accessible from Interstate 295. If it’s sunny, enjoy a pour outside on the patio. If not, the brewery itself is large and even includes an over 21 room. It’s hard to beat Swish on draft, but there are often many choices. Bissell is a good place to buy some beer to take home since you have a car.
Heading back into the car let’s get the farthest destination out of the way. This is technically not within Portland’s city limits, but it’s worth it. Drive a half-hour north to Freeport and head to Maine Beer Company. MBC is also located close to the highway. Here my suggestion would be for a flight and a pizza. Starting your journey with a full pizza is a great way to pad the marathon that will be undertaken. The beer is crisp and clean and the wood-fired pizza is light and delicious. Buy beer here too since the car is waiting just outside, especially since releases such as Dinner are hard to find elsewhere.
Back to Portland
Hop back on to Interstate 295 for the last brewery with the car. Allagash is Maine’s most well-known brewery. The Allagash White is an iconic beer that has stood the test of time. Back in Portland, Allagash is located in an industrial park that contains many breweries. Find Battey Steel, Foundation, and Definitive just across the street and Geary’s is down the road. Allagash has a slew of different beers of all styles, but it’s hard to pass up on a White from the source. If it’s nice out, try your hand at cornhole. Although many of the nearby breweries serve excellent beer, if you stop at all of these you’ll never make it downtown and you better have called an Uber.
Hotel Check In
Now that it’s mid-afternoon, check into your hotel. For a guys’ weekend in Portland, I don’t care about a fancy hotel, just something clean and comfortable. The Hampton Inn Portland West has worked out well. It’s not too pricey and a fifteen or so minute ride to downtown. Other choices include the Holiday Inn and the H2Suites located close to the airport if that suits you better. It’s the same idea though: clean, and easily accessible.
After relaxing for a few, grab an Uber or Lyft and head into town. I recommend starting in East Bayside. This neighborhood is teeming with breweries too. We’ve been to a bunch over here, but one that stands out as far as atmosphere is Austin Street, located in a former service station. Austin Street has a cool vibe inside and games to play or fire pits outside. At this point in the journey, it’s time to check the ABV for the beers. No Double IPAs!
Just next door, Rising Tide also has a comfortable feel. You can get a tasty beer that’s not too high ABV. Sip it while enjoying the sunshine, sitting at a picnic table outside, or heading inside to one of their two rooms. Keep going around the block to Belleflower for the last of the breweries here. Although their standard and double IPAs are tasty, stick to as low ABV as they serve by this point in time.
Dinner and Beyond
My suggestion for dinner would be Duckfat. Try to belly up to the bar at their restaurant or if it’s a nice night, try the Duckfat Frites Shack. The fries are delectable, and comfort food like fries sounds good just about now. Try a sandwich or if you’re feeling crazy, make your fries into an order of poutine. These are Belgian Frites; choose from an array of dipping sauces. If you wanna be like our friend Dan, order a Pinot Noir while noshing on some frites.
Round out your night at the subterranean Novare Res Bier Cafe. This is a cool spot. Often there’s a selection of Belgian beers and many hard-to-find selections from prestigious breweries from near and far.
For a nightcap, I suggest a Coors Light or a tall glass of water at $3 Dewey’s, a divey bar, very different from most of our stops thus far. Come here for the popcorn. It’s free and at this point in the evening, you’ll need all the sopping up of liquid you can get. Be careful of the walk through the Old Port’s cobblestone streets; they’ve taken down many a wobbly man! Outside of Dewey’s, call your Uber for a trip back to the hotel. A recommendation from one weary sailor is to order a second pizza of the day once at the hotel, preferably a mushroom pizza from Domino’s. The brewery portion of our guys’ weekend in Portland has (mostly) concluded.
The Next Morning
After fueling up on hotel breakfast and black coffee, it’s time for another round of breakfast. Head back into town in your car to Standard Baking Company. Try an array of excellent pastries such as morning buns and a selection of croissants. After indulging, head for a walk around a quiet Old Port, just waking up. Right next to Standard Baking is Old Port Spirits. If you liked any of the beers you tried last night, this is the place to stock up. They also sell by the can.
To Stay or Not to Stay
Given our quest to be efficient with time and mindful of our spouses/partners, we try to keep this trip at a little more than 24 hours, heading back to the South Shore and arriving back just after noon.
A Bonus Afternoon
If you’d like to extend your stay for the day and get back in the evening, this itinerary creates more like a 36-hour trip. Here are a few recommendations.
If the Portland Sea Dogs are playing (Double-A baseball team for the Boston Red Sox), I highly recommend catching a game. If your trip is from Saturday to Sunday, then the team will have a day game on Sunday. Hadlock Field is a fun atmosphere, so grab some cheap bleacher seats and cheer on the home team.
A visit to the Portland Head Light in Cape Elizabeth is another option in case your trip doesn’t align with a Sea Dogs home game.
After the game, walk along the Eastern Promenade which is gorgeous any time of the year. This park provides an ample view of the harbor. If you’re here in the autumn, the trees will be spectacular with views from this park, as well as around Cape Elizabeth.
Before you leave town, grab one last meal. One suggestion would be Nonesuch River Brewing Company in nearby Scarborough. It’s a brewpub with pub grub and a selection of their own beers. (By this time I think you’re ready for one.) It’s an easy spot in the suburbs with plenty of parking.
Raise a toast to an excellent guys’ weekend in Portland! Cheers!
What are your favorite places to go in Portland?
