Four friends and I take a yearly trip to Portland, Maine. It’s a quick turnaround as the whole event lasts roughly 26 hours. Each year, we try to change our itinerary or come up with a new theme. Always, though, the target is breweries. Our 2025 Portland Guy’s Weekend was defined by two elements: making Allagash Brewing Company a priority and dealing with the forecast calling for steady rain.
During each of the trips, there’s been some kind of new wrinkle, often involving the game “Left, Right, Center.” For this one, the winner would be awarded $100 to spend on merch. Here’s the caveat: it HAD to be spent on this trip, no saving this for scratchies back in Massachusetts. Also, if the winner wishes, he could also spend some of his merch money on his friends.
Maine Beer Company
There was only one year when we skipped the venerable Maine Beer Company. And boy was it missed! MBC is the perfect first stop, even if it’s located roughly a half hour north of Portland, in the town of Freeport. All five of us ordered a wood-fired pizza and either a flight or a single beer. The pizza is mixed and matched, where we all end up literally eating a whole pie each. It’s always delicious, both the beer and the pie, and also gives us a hearty base for the upcoming stops.
Bow Street Market – Freeport
Just down the street, we had to check out Bow Street Market. This excellent grocery store is known to get shipments of Russian River Brewing beer, including Pliny the Elder and Blind Pig. No dice this time, but it didn’t hurt to check!
Allagash Brewing Company
Off to our next destination, Allagash, the Old Faithful of the Portland brewery scene. We were especially hyped to visit on this occasion since we were given a free round at the brewery! Due to the poor weather, there was no outdoor cornhole on our agenda. Inside the brewery, we went, freshly poured Allagash White in hand. We enjoyed our gratis beer inside the actual room where the beer is brewed.
Bissell Brothers Brewing
Our last stop before heading to the hotel was Bissell Brothers. After parking, we paid our respects to Bigfoot for the last time as the International Cryptozoology Museum would soon be heading north to Bangor. With delicious Swish on draft, the five of us found a high-top to stand around on the balcony. Of all of my times at Bissell, I had never been up there. It was cool to see the perspective from the top down.
Hilton Garden Inn – Portland Jetport
Instead of our usual Hampton Inn Portland West, this year we opted for the Hilton Garden Inn by the airport. Despite an odd parking arrangement (a private company owns the lot, so there’s a separate fee to pay), this hotel worked out perfectly. It’s in a good location with easy access to the suburbs and downtown. The rooms are clean and comfortable.
Novare Res Bier Cafe
Novare Res was part of our maiden Portland guys’ trip voyage in 2022. For one reason or another, we hadn’t been back! Shame on us because this place is just so cool! It has a similar vibe to the excellent Monk’s Cafe in Philadelphia. There are so many tremendous beers on draught and in bottles. We wanted to make sure this was our first stop downtown, since this would be the last destination for drinking something higher ABV. After a round of Pliny the Elder, we all split three glasses of an Alchemist beer I had never tried… or had even heard of. The subterranean feel fits the rainy day perfectly. After toasting the brotherhood, it was time to brave the blustery wind and pouring rain.
Argenta Brewing Company
After looking at the weather for the week, I had to act fast. Our usual stroll around the city wouldn’t be so fun on a stormy day. We often bounce from brewery to brewery in the East Bayside neighborhood, to places including Austin Street, Rising Tide, and Belleflower. Not this time! I looked at where we could get the most bang for our beer buck. In the West Bayside neighborhood, literally housed in the same former industrial building were Argenta Brewing, Batson River Brewing and Distilling, and Wilson County BBQ. Sold! Not only would it keep up the driest, but we had never been to any of them.
I had recently been in touch with the owner of Argenta regarding a brewery logo article I was writing. He’s from the Southwest and brings a slice of that to this only-lager brewery. It’s got a cool old-west-type vibe to it. We saddled up like five cowboys in Tombstone, Arizona. Instead of participating in a gun fight, we opted for a lager and watching the uber popular Portland Hearts of Pine soccer match on TV.
Batson River Brewing And Distilling
From the Old West to glitzy Manhattan, or at least that’s what it felt like just a few doors away from each other. Batson River is a brewery and distillery with a few Maine locations. This place is gorgeous inside. It’s classy; the decor is stunning, as it wouldn’t seem out of place in New York City. The bar itself is huge. Most of the crew chose an IPA, while I opted for a flight. It was a nice place to sip and enjoy the surroundings.
Wilson County BBQ
From Arizona to NYC to Tennessee, our last stop was Wilson County BBQ. Boy, did they have a stellar beer menu as Pliny the Elder battled alongside Trillium and other heavyweight favorites. At this time of night, though, the lower the better as a sessionable IPA was my choice. Most of the crowd chose the handheld fried chicken sandwich as it was satisfying and filling.
And you ask, what did our good ol’ buddy Dave, who won the game, spend his merch dubloons on? A hat at Bissell Brothers and then, swag at.. Standard Baking Company. As per tradition, the next morning, we ventured back into the city for an exquisite baked good or two at Standard Baking. Dave also left with a hat and a T-shirt.
Our 2025 Portland Guys Weekend was another for the books. We braved inclement weather and still had an excellent time. With only seven stops on the tour, we were less the road warriors of some years past. We revisited an old pal at Novare Res, said hello to the trip staples of Bissell Brothers and Maine Beer Company, and even tried a few new places at Batson River and Argenta Brewing. And best of all, a round from our friends at Allagash! Cheers!
Portland Guy’s Weekend 2026
A year later, we were back at it. Unlike the driving sheets of rain from 2025, our 2026 trip was the antithesis; the day was simply gorgeous. There’s no need to rehash the whole day since a portion of it remained the same. But what I will highlight are the destinations that were new to us on this journey.
To throw a monkey wrench into the planning, we all picked one place that was our “must-visit”. Selected through an NBA-style draft, each member of our group declared their destination in order. No repeats, though, so a second choice needed to be thought of just in case. Through this activity, we were to venture to new sites, including Camp Pennant, Luna Rooftop Bar, Maps, Lincoln, and Brickyard Hollow Brewing. Leading up to the trip, Novare Res was thought of as an absolute visit. Due to the stunning day, we skipped it to stay outdoors as much as possible.
As it was our fifth anniversary, Team Captain Mike thought of all things wood-related, as wood is the proper gift for the fifth. This included on our joint playlist a track from the Wood Brothers and all of us taking home a bottle of Woods and Waters IPA from Maine Beer Company.
The adventure once again began at Maine Beer Company. The special treat this time was the ability to purchase the highly coveted beer, Breakfast. “Left, Right, Center” was won by D-Pow, who had to spend his winnings at MBC. He left with a new sweatshirt and generously treated his comrades to an MBC beer glass each. Next, Bissell Brothers proved to be a pivotal stop, basking in the sun’s rays while sipping on a Swish and a Substance as we mourned the demise of Bigfoot. Afterward, we once again returned to the Hilton Garden Inn for this year’s lodging.
Austin Street Brewery
After taking an Uber to town, Austin Street was our first stop. It’s a perennial fave with the easy-drinking Patina pale ale on tap. During this weekend, the brewery celebrated its lucky 13th birthday with live music, stickers, and outdoor activities. Always a fun time! And we even found ourselves on their Instagram page.
Apres
Although we had to skip Austin Street last year, we had been there each of the previous years. Apres, though, was new to all of us. Pivoting a bit from our typical brewery, Apres makes its own hard seltzer. Three of us tried the seltzer while the other two opted for Lawson’s Little Sip, which was available on draft. There is ample outdoor seating, and on this beautiful day was the perfect spot. Two of our crew even indulged in a Jello shot!
From here, we had to diagonally cross the city of Portland from the East Bayside neighborhood to the Old Port waterfront to reach our next destination, the Luna Rooftop Bar.
Luna Rooftop Bar
D-Lee with the classiest pick of the night as his draft pick took us high atop the Canopy Portland hotel. We may have been slightly underdressed, but no one batted an eye. Sipping a Sebago Frye’s Leap IPA with harbor views couldn’t be beat.
Camp Pennant
Another newbie on the list was Camp Pennant. The former Liquid Riot and, before that, In’finit Fermentations spot is right on the waterfront. It’s got a cool vibe with the brewery and distillery tanks on view. We settled for a round of IPAs and enjoyed them on the back deck. This was my pick.
Lincolns
A speakeasy off of Market Street, as I will not divulge any further location information. This place is so cool. Open a random door and viola! With pictures of Abraham Lincoln adorning the walls, the place lives up to its name. But not just Honest Abe, everything on the menu- beer, wine, cocktails – all cost $5, or a Lincoln. As Doc chose this spot, he hoisted a round of Fiddlehead IPAs to cheers. Cash only!
Sorry, D-Pow, at this late juncture, we never were able to make it to his choice, the very cool-looking Maps Bar.
Brickyard Hollow Brewing
For Mike’s pick, it was for dinner and a round at Brickyard Hollow. This was a new place for all of us except Dave, the Portland pro. The food here was perfect for what we needed. Sandwiches and other handhelds, or a variety of rice bowls, with folky covers of John Prine performed by a live musician. The chicken sandwich was highly enjoyable, paired with a flight of the brewery’s beers.
The group was hoping to end the night at Shipyard Brewing Company, but we were fifteen minutes too late, as the brewery closes at 8:00. Instead, it was one last MBC Lunch at the hotel bar.
Our 2026 Portland Guy’s Weekend was a blast, a fitting occasion to raise a pint for our wooden anniversary year.
2025 and 2026 were complete opposites in terms of weather, but both were memorable trips to one of my favorite cities. Similarly, each year brought our version of the Fab 5 to new locations. Cheers!
