Bar manager Evan Helwig in the Chamberlain Bar at the Cumberland Club. Photo courtesy of the Cumberland Club

This Thursday, Jan. 28, is my birthday, and since I can’t celebrate the traditional way this year, I thought I’d take us on my dream Portland pub crawl, in which I hit seven watering holes in the week leading up to the big day. This fantasy assumes there’s no pandemic disrupting the hours of operation and menu choices/specials, so please check with individual establishments about their current situation before trying to replicate this extravaganza.

I’d kick things off the Friday before my birthday at the Cumberland Club. Am I a member? No. But that wouldn’t stop me from asking a friend who’s a member to let me accompany them so that I could order a cocktail from bar manager Evan Helwig, who can somehow fill a martini glass to the rim without spilling a single drop.

The bar inside Old Port restaurant Via Vecchia. Photo by Anthony DiBiase Photography

On Saturday, I’d indulge my love of trying new places and head to Via Vecchia, where my friends are raving about both the breathtaking interior and the cocktails. Via Vecchia suggested I order its brand-new $14 Coney Island Sunday (rum, coconut gin, Earl Grey coconut cream, pineapple, orange and Italicus, an Italian bergamot liqueur). I’m also intrigued by the $13 The Smoking Mirror (mezcal, Alpine pine liqueur Zirbenz, passion fruit, vanilla foam, and Pasubio, a Dolomite Amaro).

One of my favorite Sunday spots is The North Point, home of the best pear martini I’ve ever had. I discovered The North Point on my second visit to Portland to explore whether I wanted to move here. I was wandering through the Old Port while snow fell when I heard some soft music and saw a charming little doorway. I sat at the bar and ordered the $13 pear martini (2 ounce Absolut Pear vodka, 1 ounce lemon juice, ¾ ounce pear puree and ¾ ounce simple syrup), then struck up a conversation with a lovely couple in the process of moving to Portland from California. Three years later, we’re still friends. Added bonus? The North Point donates $1 from the sale of every pear martini to help end child hunger in Maine through Full Plates Full Potential’s FEED KIDS program.

In pre-pandemic times, Bar Guide columnist Angie Bryan, right, enjoys a pear martini at The North Point with friend Rebecca Dunham of Freeport. Photo courtesy of Angie Bryan

Mondays are for Martini Monday at the Armory Lounge, the spacious library-themed bar at the Regency Hotel. It’s hard to resist a $7 cocktail, and they have a full page of options. I usually switch things up on each visit, but for my birthday week, I’d obviously have to order the chocolate cake martini: Stoli Vanil, crème de cacao, Frangelico and Bailey’s.

Tuesday requires tacos to accompany my cocktail, so I’d go to Bird & Co. and order the $10 Old Port Fashioned. Their margaritas are the best I’ve had in Portland, but I can’t resist their twist on an Old Fashioned: 2.5 ounce Maker’s Mark, 1 ounce house-made honey syrup, 3 dashes cherry bitters, and 3 dashes walnut bitters.

Wednesday (or, as I like to call it, Birthday Eve), I’d seek out Liz Smith, bar manager at Black Cow on Exchange Street, for a Bartender’s Choice – in other words, make me whatever you think I’d enjoy.

Katahdin bartender is Winnie Moody. Photo courtesy of Katahdin

My actual birthday would be at Katahdin. I celebrate all my special occasions there, but it’s also where I go when I need an attitude adjustment. Chef/co-owner Becky Simmons is phenomenal, as is bartender/co-owner Winnie Moody, who not only knows everybody’s name, but also introduces people, forming a miniature community at the bar. It doesn’t hurt that her Cosmos are the best I’ve had. I thought about asking for the recipe for this column, but decided to keep a little bit of the mystery intact.

Angie Bryan is a former diplomat who is enjoying getting acquainted with her new home in Portland, one cocktail at a time.