The Wayfarer’s Digest: A Travel Guide Through Locals’ Eyes

Thinking of a Fall Break destination or a weekend jaunt that’s within driving distance of Wesleyan? Portland, Maine may be your best bet. A mere four-hour drive from campus and two hours north of Boston, Portland is Maine’s largest city, both charming and historic, set on a picturesque peninsula protruding into beautiful Casco Bay. With a myriad of art galleries and a top-notch locavore cuisine, the laid-back city is the ideal spot to rejuvenate after midterms before the daily grind sets in once again. Advice from three Portland natives offers insight into how to enjoy the city at its fullest.

Shops

The best way to get a feel for the city is to walk it. Robin Mitchell ’13, a Portland native, enjoys the antique streets of the Old Port that are closed off to traffic.

“They didn’t pave over the cobblestone streets, so there are streets that cars can’t get through,” Mitchell said.

Discover the Old Port’s historic homes and boutique shops, fine dining and abounding coffee shops. If shopping is what you’re after, don’t get sucked into the expensive touristy boutiques.  Instead, you’re better off looking through the thrift stores that surprisingly offer unique pieces at reasonable prices. Tess Crain ’12, who attended high school in Portland, cites Encore and Material Objects, both located on Congress Street, as two of her favorites.

“Encore is right across the street [from Material Objects],” Crain said. “You can get the best designer shoes and jewelry there for really cheap.”

If you’d like to get off the main (no pun intended) drag, head uptown a few blocks from the waterfront to the Arts District, which features art galleries, artist studios, and antique shops, as well as the Portland Museum of Art. It is the oldest and largest museum in the state and features American art, furniture and crafts, as well as European works.

Of course, the L.L. Bean store is synonymous with Maine, so its no surprise that its factory outlet store is located in Portland. Prices here may even be lower than in the original Freeport location, which is just a twenty-minute drive away and is open 24/7, 365 days of the year.

Bull Moose Music, on Middle Street, has a great selection of new and used music, DVD’s and vinyl records, and is very popular among locals.

“I can’t go into Bull Moose Music without bumping into at least eight people I know,” said Aaron Peisner ’12, another native Portlander.

The Portland Head Light and Museum, just a fifteen-minute drive from downtown Portland, is a lovely lighthouse and a Maine icon. Or, if you’re visiting in the summer, catch a Portland Sea-Dogs game.

“It’s a really cheap and really fun thing to do,” Crain said.

Restaurants

All of that walking is likely to stir up an appetite, and Portland offers many enticing culinary choices and scores of coffee shops.

“Coffee shops are a huge Portland thing,” Crain said. “I used to work at Others’ coffee shop (15 Monument Sq). It’s fair trade, organic coffee – it’s very Portland.”

While Portland boasts restaurants with cuisine from all over the world, if you’re in Maine, you’re pretty much required to have lobster. Peisner recommends the Lobster Shack in Cape Elizabeth that’s on the water and next to two state parks. Price however, may be a deterrent.  For a more relaxed environment, he suggests Flatbread and Co. (72 Commercial St.) as another excellent place to eat.

“It has really fresh ingredients and a really good atmosphere,” Peisner said. “It’s one of my favorite places to eat in Portland.”

And for an unconventional brunch, head to the Bayou Kitchen (543 Deering Ave.), which serves Cajun omelets among other tasty breakfast offerings. Peisner praises it as “easily the best brunch I’ve ever had.”

To top off the other recommendations, the three interviewees unanimously recommend Silly’s restaurant on Washington Avenue.

“[Silly’s] is just a really cool place with old flea market stuff on the walls,” Mitchell said, “It’s great.”

Go for one of their “Hippie Hippie” shakes, laden with peanut butter, jelly and pretzels.

Music Scene

If music is what you’re seeking, Portland will not disappoint. Peisner suggests picking up a copy of the Portland Phoenix, a local magazine, to find out about weekend events.

“The State Theater just re-opened,” he said. “It’s a really nice medium-sized venue for bands that won’t fill the Civic Center. The Space Gallery is also really good, and they’re both on Civic Street.”

If you’re seeking a truly local place with a laid-back feel, head to the North Star Music Café on Congress Street.

“It’s a good place to go – good food, good local music, a singer-songwriter kind of place,” Peisner said.

Crain also recommends The Station and the Big Easy, located on John and Market Streets respectively, if you’re looking for smaller music venues. The Asylum, on Center Street, is another choice, if you’re looking for a different sort of atmosphere.

“[The Asylum]’s like a club. Picture the O.C.”

For local bars, head to the cobblestoned Fore Street, which Peisner claimed can get crowded on weekend nights when tourists flood the city.

Just one word of warning: don’t expect to find any late-night munchies in this town.

“There’s nowhere to go to eat after midnight other than, like, Denny’s,” Peisner said.

We recommend taking a “Hippie Hippie” shake to go so you’re well-fueled for any Portland adventures.

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