October 2016 | view this story as a .pdf

If you’re working after hours, why not make it somewhere special?
Discover the best places in the city to seal a deal over a drink.

By Karen Hofreiter

It’s said that the most important business is conducted on the golf course, not in the office. But when the weather turns chilly, you’ve got to bring your A-game indoors. Luckily, Portland is home to a host of savvy restaurants and bars perfectly suited for mixing cocktails and contracts or dinner and deals.

Where the Closers Go

No one knows the best places to woo clients better than Portland’s top professionals. For John Hatcher, owner of The Hatcher Group of Keller Williams Realty, the Cumberland Club means a done deal. “The Cumberland Club is one of Portland’s undiscovered jewels where I can meet with clients in a discrete location in the heart of downtown. The food is outstanding–the lobster BLT is the best lobster sandwich in Portland–as well as the craft cocktails and signature drinks. The staff knows every member’s name, and my guests are always made to feel special.” From the Club’s impressive white-columned entrance to its stately Victorian-style dining room and bar (complete with chandeliers, fireplace, and crown molding), one can smell sweet success. The Club offers private meeting rooms, three cozy living rooms, and the “Chamberlain Bar” named for Joshua Chamberlain who was a member of the club.

Nicole Olivier, author and owner of the literary events company BookSpeak, likes to keep it casual and low-key. “It’s fun to talk books with an author at the Hunt + Alpine Club, with its crisp, Scandinavian atmosphere and cleverly crafted bartending. Their cocktails also honor the ’50s with a twist, not to mention their windows on Tommy’s Park and people-watching if you sit at the counter, waiting for your guest to arrive. For a quiet, cozy neighborhood feel, definitely [head to] the Treehouse Cafe and Lounge.” Olivier recently met with Ann Beattie (The State We’re In) at Pai Men Miyake on Longfellow Square.

Small, quiet and a bit off the main drag” is how Tom Landry, broker/owner of Benchmark Real Estate, describes his favorite places to charm clients. “For a quick meeting with drinks and apps, it’s Lolita in the East End. It has a great local beer selection and inventive cocktails (clients love the Boss Lady II). The staff knows me and is always polite, helpful, casual, and welcoming–a rare blend. If I really want to impress and have time for dinner, it’s off to my new absolute favorite: the Drifter’s Wife. Owners Peter and Orenda Hale and the staff are among the most knowledgeable of food and beverage of anywhere we’ve dined. Clients are always impressed by the simple, ingredient-centric dishes.”

Other favorites for sophisticated schmoozing include the Top of the East, with its spectacular panoramic city views and decor that reminds us of a hotel in Reykjavik, so it may be the perfect spot to negotiate with our Eimskip friends; the indigo-hued, modern and airy Glass Lounge; and the sleek and studious Inkwell (pictured previous page), where contracts are certain to get, well, inked.

Toast of the Town

If it’s potential clients, partners, or just like-minded industry folks you are looking to meet, Portland’s numerous lively networking events are the way to go. Events hosted by the Maine Women’s Network are a great example of what can be expected: top locations (e.g., Portland Country Club, Top of the East), light hors d’oeuvres, and a large crowd of all ages representing a wide range of industries (corporate, healthcare, education). “Our organization is about women supporting women to grow their professional and leadership skills through networking and education. Attendees have really enjoyed the speakers we feature and love the open networking event. It’s an opportunity to create collaborations,” says Kris McCrea, Chair of the Portland Chapter MWN.

Many networking groups are tailored to certain interests; for example, Greendrinks is for those with an interest in sustainability and the environment, while Think Local is especially for individuals and small businesses and spotlights local non-profits. Young professionals will want to check out PROPEL, which hosts themed events including “Welcome to Maine” for newcomers; “Portland Eats!” for foodies; and “Live from the C-Suite” for picking the brains of the top execs in town. Portland Regional Chamber of Commerce events are key to getting to know the movers and shakers in the local business community. 

The Cumberland Club: 116 High Street, Portland, 773-6402, membership required

Hunt and Alpine Club: 75 Market Street,
Portland, 747-4754

Treehouse Cafe and Lounge: 484 Stevens Avenue, Portland, 874-0706

Lolita: 90 Congress Street, 775-5652,

The Drifter’s Wife: 63 Washington Avenue, 805-1336

Top of the East: Westin Portland Harborview Hotel, 157 High Street,
207-775-5411

Glass Lounge: Hyatt Place Portland,
433 Fore Street, 207-775-1000

Inkwell: 119 Exchange Street, Press Hotel, 207-808-8800

Maine Women’s Network: open networking evening events the 3rd Thursday of
every month.

Greendrinks: second Tuesday of every month, 5:30 p.m.

Think Local: Business Mixers.

PROPEL: After Hours events.

Portland Regional Chamber of Business: “Business After Five” events.