January 1, 2022

Where to Go in Portland, Maine For Date Night This Winter

Originally published in Maine magazine, January 2022

The challenge of eating outdoors last winter was sometimes fun (and necessary), but this year I’m ready to go back inside where it’s warm. Let’s reconnect with loved ones over a shared meal, surrounded by the pleasant buzz of strangers enjoying a night out. Maine has so many destination restaurants, so here’s a pared-down list of nine worthy spots for when you need to shake up your “Netflix and chill” routine. Ditch the sweatpants and put down the takeout menu: we’re going out. 

Joshua’s | 1637 Post Rd. Wells

Cozy up with some farm-to-table fare at this restaurant located in a restored 1774 Colonial-style house on Route 1 in Wells. Chef Josh Mather serves upscale American dishes using many ingredients grown nearby on his parents’ farm. The dining room is partitioned into several small rooms, providing plenty of intimate corners in which to enjoy your meal. Share a dish of wood-grilled mushrooms with truffle butter to start, and don’t miss my favorite entree: roasted haddock with caramelized onion crust served over mushroom risotto.

The White Barn Inn | 37 Beach Ave. Kennebunk | whitebarninn.com

This luxury inn’s restaurant is regularly voted one of Maine’s most romantic dining spots, and for good reason. With white tablecloths, a huge window that overlooks trees wrapped in twinkling lights, and even a piano player, the setting is primed for romance. Classic Maine dishes have luxurious touches, like caviar atop the lobster roll and sherry-laced lobster bisque. The Little Barn offers a more casual environment with a bistro menu, but you may find yourself envious of the diners in the main dining room.

North 43 Bistro | 1 Spring Point Dr. South Portland | north43bistro.com

For the best view of the Portland skyline, venture across the river to South Portland’s Ferry Village neighborhood. The window-lined dining room overlooks Spring Point Marina, and the expansive menu offers dishes for everyone, from boar bolognese to miso-ginger-glazed salmon. A date night at this waterfront bistro will make you feel like you’ve gotten farther away than just South Portland.

Chaval | 58 Pine St. Portland | chavalmaine.com

With its warm lighting and French- and Spanish-inspired cuisine, Chaval in Portland’s West End is a great date-night destination. Don’t miss the starters, like the simple pan con tomate or trumpet mushrooms with chorizo and duck egg. Entrees like swordfish a la plancha and coq au vin are hearty wintertime favorites. For a truly special evening, reserve one of the heated greenhouses on the patio and enjoy a private meal in comfort.

Via Vecchia | 10 Dana St. Portland | vvoldport.com

Between the glam decor and the standout cocktails, a visit to this Old Port restaurant makes for a memorable evening. Velvet-lined banquettes and leather club chairs offer comfortable seating in the front bar area, while the mezzanine in the back provides a more intimate environment. Tropical cocktail lovers won’t want to miss the Averna Mai Tai, and there are a variety of housemade pastas and flatbreads perfect for sharing.

Evo Kitchen + Bar | 443 Fore St. Portland | evoportland.com

Sit at the chef’s counter at this buzzy Mediterranean spot in the Old Port to watch the kitchen prepare modern takes on classics like baba ghanoush and chicken shawarma. Tables in the upstairs dining room offer more privacy for enjoying small plates of the restaurant’s signature chickpea fries and bluefin tuna crudo. Don’t miss dessert at Evo—pastry chef Maureen Hobby’s creative sweets are perfect for sharing.

Water Street Kitchen + Bar | 15 Water St. Wiscasset | waterstreetmaine.com

With big windows that overlook the Sheepscot River from its enclosed porch, Water Street Kitchen and Bar’s ambiance creates the right conditions for romance. Chef Ed Colburn serves a menu featuring plenty of Maine seafood with French, Italian, and Spanish influences, like roasted lobster with tarragon butter and a shellfish paella. The recent renovation of this property makes it a great destination for a romantic midcoast road trip.

Nina June | 24 Central St. Rockport | ninajunerestaurant.com

This Mediterranean restaurant from chef Sara Jenkins is located in charming Rockport, which feels like a getaway all on its own. The restaurant has great views of the harbor from its dining room, where a four-course prix fixe meal made up of Italian, Spanish, and other Mediterranean dishes is served. Enjoy the same ambiance with a more casual menu in the cafe seating. Take home a memento from the selection of imported groceries, like tahini, olive oil, or dried pasta.

The Fiddlehead Restaurant | 84 Hammond St. Bangor | thefiddleheadrestaurant.com 

Diners in Bangor love this casual yet elegant spot for its farm-to-table fare and extensive list of unique cocktails. With exposed brick and hardwood floors, the restaurant has a cozy vibe that will warm you up on a winter night. Start with a plate of local cheeses, duck rillettes, and housemade tomatillo jam, or marinated mushrooms over farro. Entrees like vegetable chow mein and lamb tamales reflect the global influence of chef Melissa Chaiken’s international childhood.