Who says the weekend ends on Sunday?

September 2018

By Olivia Gunn Kotsishevskaya

Portland, meet Monday. You’ve made it through the first eight hours of the work week. Now, let’s have some fun on a night that dares you to go out on the town.

Join The Inkwell at Portland Press Hotel for their Off the Record Happy Hour. The $5 house wines, well drinks, and 16-ounce local beers lure you in, but the real draw is basking in that early evening sun. The Inkwell’s cool, minimalist interior and white marble bar are designed to offer a crisp start to your evening.

The “shares” menu includes easy snacks like the House Made BBQ Chips ($7) and Grilled Flatbread ($12). Looking beyond the well, enjoy one of the signature cocktails, including the Lime Rickey ($6) or the Szechaun Gimlet ($12), a peppery vodka sip sure to give you the kick you need before making your way to Monument Square, where a fabulous dinner awaits.

A Monumental Meal

Few seats in town beat a high-top table at David’s Restaurant. A window seat showcases the city in motion.

Start off with Daily Mussels, which on a recent visit were smothered in a tomato basil broth. You may be hesitant to soak the rest up with fresh garlic bread on your romantic evening, but trust us. Life is too short to not indulge. Just don’t forget the Doublemint.

Soon you’ll be on the dance floor, so keep the meal light with a shared Napoletana Margherita pizza ($23) and the Arugula & Beets Salad ($13.50). The entire meal proves you don’t have to break the bank to enjoy a decadent date here.

Feel the Funk

Now that you’re fed, full, and hopefully a little tipsy, it’s time to soar on the dance floor of Portland House of Music and Events. Gina & the Red-Eye Flight Crew crank up Monday nights through September 24. From 8:30 p.m. to midnight, the band has all you need to step out of the Mondays and dance your way into the week.

There’s no room for wallflowers at this party, so the two of you had better be prepared to move. The floor is packed by 10 p.m. It’s clear some people wait all weekend for this. But don’t worry, no one is here to judge. You’ll see dancers of all styles getting down to Stevie Wonder like there’s no Tuesday in sight.

Whiskey and Chill

Before calling it a night, take the four-minute walk to the newly opened Independent Ice Co. on Wharf Street. This cozy, leather-seated bar has enough space to get comfortable and close, and the chandelier and candle lighting offer the ambiance you need to start taking flirtations a little more seriously.

Cool off those dancing shoes with one of the “Pure Pours.” The Knickerbocker Ice Boulevardier ($11) is the nightcap you need. The bourbon-based cocktail with a touch of campari, sweet vermouth, and orange peel is the final answer to this night and hopefully loosens you up just enough to ask, “What are you doing Tuesday?”