While Portland, Oregon may be attracting culture vultures from all over, Portland in Maine happily flies under the art radar, attracting only the savviest of art oglers.

Art aficionado Daniel Kany has worked in hipster hubs across the US. Now he's back in his home state of Maine, and with good reason: Portland is stepping up to bat with plans to hit an artful home run. So we've created an all-star line-up of activities based on Daniel's insider tips.

A visit to the Portland Museum of Art, near Congress Sq, is a must before one begins a gallery gallivant. This first-rate museum, designed by illustrious architect IM Pei, is the crown jewel of Portland's thriving art scene. The modern gallery spaces feature a slew of notable American artists like Edward Hopper, Rockwell Kent, Andrew Wyeth and Winslow Homer (a Mainer). Be sure to check out the temporary exhibition hall, which usually houses the thematic works of heavy hitters like Georgia O'Keefe.

After exiting the museum, head to Susan Maasch Fine Art – also on Congress St. Here visitors will find an impressive assortment of big names like Picasso, Robert Mapplethorpe and Ansel Adams. Have a chat with the owner and curator, Susan Maasch, who often gives the impression she's had a few espressos before bouncing in to work.

The two June Fitzpatrick galleries are also great spots. The space on High St features only works on paper, and the other space, squished among the storm of competing galleries on Congress St, partially serves the Maine College of Art (MECA). A Londoner by birth, June maintains her British accent with regular trips back to the motherland to run a drawing studio.

June brings an old-meets-new vibe to her spaces – don't be surprised to find a clay pot next to a digital process installation piece.

Stepping off Congress St into Whitney Art Works feels like entering a transporter and being zapped to Soho or Chelsea. This happening space focuses on cutting-edge sculpture, 2D and installation works. But don't be fooled; these bizarre pieces, including sculptures made from books and 'surveillance sandwiches' (you'll see), are the brainchild of local artists.

Take a quick detour up Preble St and onto Portland Sq to Walter's (2 Portland Sq). Pause for lunch in the narrow storefront-cum-dining room and taste test the bouillabaisse or the succulent fish tacos. One last gallery stop before becoming 'art-ed out': Greenhut Galleries, in Middle St, is Portland's first private gallery and the anchor of the city's progressive art scene. The kind staff members at Greenhut curate work in an intimate and friendly place and focuses their efforts on showcasing masterpieces by some of Maine's most accomplished artists, including John Whalley, a favorite among local gallerinas.

Turn your arty adventure into a complete sensorial experience at Bresca on Middle St, Portland's hottest dining option. The duck breast with nectarines is a local favourite, and the chorizo- and gorgonzola-stuffed dates will bring a tear to your eye. Like any other see-and-be seen joint, this charming, jewel-box-sized restaurant is almost always full (because there are only five tables), so reservations are highly recommended. If you can't score a spot at Bresca, try Fore St, which is arguably just as good. Owner and chef Sam Hayward has made apple-wood grilling and roasting his forte. The menu changes nightly, and features the best seasonal fruits of the land and sea, not to mention the most comprehensive wine list in town.

A late-night stroll is an absolute must after gorging on scrumptious fare served in intriguing positive-negative schemes. Casually work off those calories while moseying down Wharf St and let the eclectic mix of live music and lounge chatter wash over you. Weekends in the heart of the Old Port bounce with a colourful clash of locals and weekenders, while weekdays tend to be a bit more slow-paced, fostering the ultimate mellow vibe. Sample some chilled-out bluegrass beats at a Local 188 up on Congress St, or loosen your belt (in the name of art, of course) and make room for a heavenly dessert at Five Fifty-Five.

As the evening comes to a close it's time to retreat back to your wooden four-post bed at Portland Harbor Hotel on Fore St for comfy sleep amid soft linens and fluffy pillows. But don't rest too easy, intrepid traveller; even though your avant-garde adventure is indeed ahead of the curve, you've just started to scratch the surface of the city's hidden boho culture. Hopefully you've planned to stay a second day here in the better of the two Portlands…

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