Your guide for a night you’ll never forget.

Winterguide 2020

By Sofia Voltin

Grab the timeless dress that’s been gathering dust in the back of your closet. Tonight, sweep your date right off the couch. We’re going out.

“I send couples to start the night with a drink at Top of the East,” says Madalyn Eliason of the Portland Regency. The sophisticated rooftop lounge atop The Westin has floor-to-ceiling windows with panoramic views and cozy seating. Set the mood with It’s Complicated ($13), a signature cocktail with gin, vermouth, and Fernet Michaud. It’s “promiscuous, inquisitive, and a little minty.” Cheers to the night and take in the sights of our sparkling city.

Fancy flickering candlelight? “Back Bay Grill is one of Portland’s few white tablecloth dining options for something a little fancier,” says The Press Hotel concierge Joshua Bennett. The bronze asparagus-handled doors are the first sign that you’re in for something special at 65 Portland Street. Let the host hang your coats in a separate closet. “When people make reservations, we always ask if they’re celebrating a special occasion, especially for a party of two,” owner Larry Matthews Jr. says. “We like to seat them at a private corner table. We just had two couples in one night celebrating their 30 and 31-year anniversaries.” At your candlelit table, open the heavy black leather wine list embossed in gold. “Right now we have 220 to 250 wines,” Matthews says. Whether you split a bottle recommended by the staff, or warm your bones with a seasonal craft cocktail like the Back Bay Black Manhattan topped with brandied cherries ($15), your night is served on a silver platter. You’ll want to try the Maine Crab Cake ($19) with caramelized leek aioli, gruyere crisps, and pickled carrots. This is a night of decadence. Go for it with a Filet Mignon ($43), Rack of Lamb, ($41), Lavender Marinated Duck ($36) or Casco Bay Cod, ($34). Your night of fine dining will leave you and your date believing you’re royalty. “Some people head to the symphony or the theater after visiting us. For many couples, dinner is the show.”

Portland Stage Company awaits for a spot of romance by way of live theater. Almost, Maine runs from January 15 through February 9. The beloved romantic comedy premiered here at 25 Forest Avenue in 2004, where it broke the box-office records and went on to gain acclaim Off-Broadway. The play weaves through nine short stories exploring the joys and tragedies of love in a small mythical Maine town called “Almost.”

What’s more classy than classical music? Enchant your partner with Portland Symphony Orchestra’s Romantic Tchaikovsky January 19 or 21 at Merrill Auditorium. Don’t miss the live piano performance The Virtuosity of Joyce Yang on February 11.

Warm up in each other’s arms with a night of dancing. “Our Latin dance nights on Fridays happen every two weeks or so,” says Martha Leonard, co-owner of Maiz Portland. “They’re for partners and singles, veteran dancers or beginners. DJ Avel usually plays a mix of salsa, bachata, merengue, and reggaeton. People dance both formally or however they please.” The dates for Latin Beats and Eats at 621 Forest Avenue are announced regularly on Maiz’s Facebook page.

After all that dancing, we’re feeling a bit parched. “I would wander up Market Street for an end-of-the-night drink,” suggests Portland Harbor Hotel concierge Reggie Humphrey. “There are a few new smaller bars with a romantic atmosphere. But my favorite is still Bar of Chocolate.” Tucked away on the cobblestone Wharf Street, the dim hole-in-the-wall is a welcome break from the rowdy bar scene. Inside, the twinkling string lights and romance tempt you to warm up with a nightcap and a slice of chocolate cake ($6.50). They consistently offer eight varieties of chocolate cakes and tortes. Savor every last bite. Every moment tonight must never end.