July/August 2015 | view this story as a .pdf
You’ve done the trendy. Why not do the tried and true?
The mystical question: How can we call a watering hole one of the usual suspects if we’ve never been there? Nowadays, Portland is famous for its perpetual bloom of new bars, restaurants, and shops. But there’s a reason some places around town–friendly dives where, shockingly, you’ll find no signature cocktails or small plates–have lasted for decades. How do they keep it real?
Pizza Villa, 1965
On a Wednesday night, my friend Steph and I wrap up a shred session at the rock gym and make our way to Pizza Villa for a beer. Neither of us has ever been here before, and as we walk to the doorway (nestled next to a picture window featuring a neon beer pint and hot pink moon) we spot a handful of people inside.
We saddle up to the bar, where we meet Scott, our new favorite bartender. He’s attentive, friendly, and has worked here 11 years. While he’s pouring our $8 mini pitcher of Brooklyn Lager, I notice something funny behind him. It’s a ceramic figurine depicting a black poodle in a white sack, with a heart-shaped dog tag. I assume it’s a bank.
“The poodle?” Scott laughs and brings it over so we can get a better look. “It’s full of Jim Beam. The owners of this place are three Greek guys. Their Uncle Fred brought this thing in one day and set it behind the bar. He said, ‘When I die, I want you to drink this.’ The guy’s 96 years old.”
I examine the poodle. Its collar reads, “Tiffiny,” an appropriate name for an eight-inch tall poodle, although pretty humorous for middle-shelf, 1970s-era bourbon.
“Yeah,” Scott continues. “A few years ago–Fred had to be at least 88 at the time–I saw him roll a golf cart right over, get back up, and play the next hole.” Look for Tiffiny next time you’re there; she’s probably not going anywhere. 940 Congress Street.
Mathew’s Pub, 1872
On a Thursday evening, “Portland’s oldest pub” is empty aside from two employees, my accomplice Mitchell, and me. We sit at backless swivel stools, order $3 Budweiser drafts, and ask if the rooftop deck is open. “Oh sure, but I’ll have to give you plastic cups,” says the young bartender, pulling two green Solos from below the bar. “Can’t take these glasses?” I ask. “Yeah, people would throw them off the roof, so we don’t allow them up there anymore,” she says.
It’s quiet up there on Free Street and we sit, catching up for half an hour. On the weekends, this place can get pretty rugged, but tonight it’s just us, beer in plastic cups, and a view of a parking lot partially obstructed by a steel safety fence.
Mitchell suggests pool. The bartender hands us the rack of balls, and her colleague, probably a bouncer, warns that there is only one cue. The tables are a little lumpy and the cue has no tip, but the game is free. Even better, the pool room is also a storage area, where we admire a pile of broken jukeboxes and promotional materials, including a Bud Light Superbowl XLVIII countdown clock, to which Mitchell takes a shine. 133 Free Street.
The Great Lost Bear, 1979
This is one of my favorite spots in Portland–huge tap list, good pub food, and tchotchkes absolutely coating the walls. On a Friday night, it can be hard to find a seat at the bar or in the dining room–the secret is to navigate around the bar and find a booth around the back side–it’s all seat-yourself, and the service is quick.
The Bear is best experienced with a group. You can usually find a good-sized table, and there are plenty of appetizers, like the great and zesty nachos that are more than big enough to share. With such a huge beer selection, everyone can find something he or she likes, from fans of $3 cans of Narragansett to the biggest beer snobs in Portland.
My preferred time to get lost at the Bear is on a Monday or Tuesday night, when the pub offers “Talls for Smalls,” 23-ounce beers for the price of a pint. The crowd early in the week is smaller and more personal. The Bear is famous for hiring artists and actors; just ask Bear alums like Michael Rafkin, actor and director of many Mad Horse Theatre and Portland Stage shows, and writer/actor Elizabeth Peavey (My Mother’s Clothes Are Not My Mother). 540 Forest Avenue.
Forest Gardens, Ca. 1930
This is one definition of a hidden gem: small but diverse, with a good-humored bar staff. On a Friday night after a long day at the office, I rally my roommate Brent. “Want to go to Forest Gardens?” I call from the kitchen.
“Good enough for me.”
Our apartment is in the Oakdale neighborhood, and the convenience of Forest Gardens blows us both away. Here is a bar with $2 beer 100 yards from our front door. While the place is cash only, there are exactly three banks with ATMs along the walk there.
The pleasantly salty bartender Ray is kept busy running beers, catching up with regulars, and grilling burgers in the closet-sized kitchen off the bar.
“It’s a nice little place,” he explains. “It’s cash only, we’re only open until 11, and there’s no hard liquor. Younger people who want to go all out don’t come in here because they want to pay with plastic. They might stop in for a beer on the way into town, but being cash-only puts kind of a limit on how crazy people can get.”
We have a few rounds, and Brent asks what’s in the kitchen. The barkeep produces a menu featuring hamburgers, French fries, onion rings, chicken fingers, and even a clam burger–all under $5. He offers to make us a mixed plate. Perfect. We spend less than $20 total on two rounds and a big plate of fried snacks. 372 Forest Avenue.
Old Port Tavern, 1972
So close to the historic Mariner’s Church, Old Port Tavern is low, fun, and loud on a Saturday night. Upon entrance, it’s hard to believe this club is a former place of worship –or even that before the sun goes down, it’s a restaurant. Upstairs is a dart and pool hall, but my group is feeling adventurous so we make our way down into the basement, following the buzz of party bass lines.
Hip-hop and Top 40 music blares from subwoofers at the far end of the room, and the basement bar area is packed end-to-end with groups of 20- and 30-somethings chatting, doing shots, trying to yell over the music, and dancing.
Getting to the bar is a challenge, but I make it. The bartenders are doing their best to keep everyone happy, but they are surrounded by very thirsty patrons. My patience is eventually rewarded, and I obtain a reasonably strong whisky-ginger at a price on par with other Old Port joints.
After some dangerous and painful dancing, it becomes apparent that flip-flops were a mistake; my toes are stepped on a total of six times within an hour. We retreat from the crush to an out-of-the-way fish tank near the door. 11 Moulton Street.
DiMillo’s on the Water, 1954
While the famous DiMillo’s floating restaurant has only been on a boat since 1982, the DiMillo family has a long history in Portland. It shows in customer service and atmosphere, because DiMillo’s on the Water is one of the friendliest places to grab a drink in the Old Port.
On a rainy Sunday, I make my way down the gangplank into the repurposed Jamestown, Rhode Island ferry and grab a seat at the long bar. The dark, polished wood has a film-noir glamor and seats a good 40 or so. I grab a stool next to Chris and Kelly, a married couple visiting from Newport, New Hampshire. Chris runs a heating oil/mechanical contracting business, and Kelly’s just taken a job as a school principal.
We chat about local beer and the benefits of weekend mini-vacations, and about education, the weather, sports, traveling–the works. Even the bartender gets involved; she’s planning a trip to see her boyfriend stationed in Arizona with the Army. They are amazed to learn this restaurant even served its gorgeous lobster entrees, staying open during The Perfect Storm.
I sip on a Roulette ($9), which is a borderline Manhattan combining Bulleit Rye, Grand Marnier, and Peychaud’s Bitters. Outside, the wind blows, the rain pelts the plastic deck enclosure, and we watch the Nova Star disappear into the fog. 25 Long Wharf.
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