11 Unique Date Ideas in Portland, Maine

Photo of Christopher Crosby
4 December 2017

Headed to Portland, Maine, on a date but out of ideas? We’ve got you covered. Skip the typical and try these unique and romantic options that highlight the city’s maritime history and current culinary prowess.

See a movie – at the art museum

Art Gallery, Museum
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Portland Museum of Art | © Joe Turgeon / Flickr
Fridays after 4pm are free at the museum, so why not take your date to see French impressionists before the films start at seven? Topics vary, but the art museum offers films on topics ranging from photography to Jane Goodall most Friday and Saturday evenings for a small fee. Grab a quick bite to eat (oysters and beer?) beforehand at Street & Co. on Wharf Street.

Paint. Drink wine.

Bar, Wine
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Muse Paintbar on Commercial Street has become a date-night hotspot full of 20- and 30-somethings finding inspiration or at least Pinot Noir. Sitting before an easel, painters get how-to instructions from a real artist who prowls around the shop, ready to assist your budding Renoir (during couples night, once a month, each half of the significant other paints a portion of the same piece). With numerous bars and restaurants nearby (try Liquid Riot Bottling Company or Central Provisions), the date night can end or go on long after the paint is dry.

Reach for the stars. Or at least the next grip.

Building, Gym
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Portland Rock Gym | © Evo Rock + Fitness
Trust-building is a key component to any relationship, so why not find out if your date is truly The Right One by testing one another’s mettle from the get-go? Enter rock climbing. For $16 each, you can get a full-day’s access to Evo Rock + Fitness and try hundreds of different grip, positions and handholds (perfect for future hand-holding). Novices need not fear, there are low courses for them; experienced climbers can take the lead and use the ropes to ascend to new heights.

Arcade Bar

Bar, Pub Grub
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What better way to kindle love than indulging nostalgia and polishing the past until it glows? That’s the idea at the Arcadia Bar, where booze and arcade games from yesteryear combine. Pinball, board games and old console classics are offered, and every Friday there are lessons on how to play inaccessible veterans like Settlers of Catan. The drinks are cheap, and if you’re hungry head to Grace, an altar to food.

Flick At the Nick

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Tried and true date ideas never go out of style, especially at fashionably retro theaters like Portland’s Nickelodeon Cinemas. See popular blockbusters or aim to impress (or bore?) with indie art house films. The films are cheaper than the megaplexes, and spilling out into the Old Port isn’t the worse way to end a date or keep a new spark lit.

Farm Fresh Cooking (Done Yourself)

Farmers' Market, Market, Vegetarian
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Summer Tomatoes | © Courtesy of Mason Masteka
Do a dry-run on domesticity and cook a meal for your date using produce and meats from Maine’s farmers. Portland’s farmers’ market (every Wednesday and Saturday morning) feature a host of seasonal, local field fresh goods for cooking a romantic dine-in for two. You’ll feel good, and the ingenuity will hopefully score brownie points with your date (or, at least, brownies).

Catch A Live Performance

Forest, Theater
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If the big screen isn’t your thing, consider a live act by local Maine stage writers. The Portland Stage Company offers intimate works addressing and shaping issues affecting the communities here. The 75-seat theater hosts well-known works like It’s a Wonderful Lifebut also character studies and acts homing in on individual relationships.

Tour A Brewery

Brewery, $$$
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The samples may no longer be free, but it still costs nothing to come see Allagash Brewing Company, Maine’s premiere Belgian brewer. For more than 20 years, Allagash has been an innovator, churning out award-winning beers and pushing the envelope in terms of style and taste. The tour takes visitors past gleaming kettles, floor-to-ceiling steel storage containers and a massive walk-in cooler full of stacked barrels aging sour concoctions. You have to book in advance, and there’s a paid upgraded tour where the proceeds go to charity.

Picnic on the Prom

Eastern Prom | © karlnorling/Flickr

Come summer, Portland’s Eastern Prom is a gem for sun-seekers soaking in the rays. With views over Casco Bay, it’s also a great place for a picnic. Unfurl a blanket, spread out and enjoy an intimate conversation.

Ferry Trip

Sunset on Bailey Island | © Paul VanDerWerf/Flickr

Casco Bay teems with islands, easily explored via downtown Portland’s ferry terminal. Peaks Island — a half-hour voyage — is the most popular trip, but there are a number of options to consider. Bigger islands like Peaks and Bailey have bikes and gulf carts to rent and beaches to explore, while smaller islands like Cliff are populated solely by residents. Come New Year’s Eve, the ferry also does a nighttime harbor cruise — bring a coat.

Seafood on the Shore

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Portland Head Lighthouse | © Courtesy of Paul VanDerWerf / Flickr
Okay, while technically in nearby Cape Elizabeth, the Portland Head Lighthouse is an iconic Maine site, a landmark building at once romantic and oozing with the state’s maritime connection. Grab some fried seafood from a lobster shack and dine on the cliffs as the waves pound the shore around you.

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