Shopping Weekend Getaway in Portland, Maine

  • Distance from Boston: 108 miles
  • Best time: May to October
  • Best for: RomanticShoppingBeaches

Travel up the coast a couple of hours from Boston and the scenery starts to change, the trees becoming somehow more majestic, and the exits indicating distances in kilometers as well as miles. While Montreal is still five hours away, Maine also signals a new state of mind. Only 100 or so miles up I-95 from Boston, it's a world away from the city. Dotted with picturesque town centers and regal coastline, the span from Kittery to Freeport is an attitude-adjusting getaway—a place to find your center whether your relaxation comes from ocean scenery or generous amounts of retail therapy. – By Lisa Oppenheimer


Portland Cheat Sheet

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1 The brews flow from 11:30 a.m.-1 a.m. at Federal Jack's, a restaurant and brew pub on Maine's proud Beer Trail (see all twenty-five and you'll get a prize pack of Maine Beer Gear!). World-class ales are brewed right downstairs at the Kennebunk Brewing Company.

2 You can't miss the Colony Hotel—it stands proudly in all its grand-dame elegance along coastal Ocean Avenue. Enjoy lobster, the sunset, and the charmingly throwback ambience. Dress rules are no T-shirts and no tank tops. You'll want to make reservations ahead.

3 Goose Rocks Beach ups its hip quotient with the arrival of The Tides Beach Club hotel and restaurant. The bar hosts pretty people every night 'til the wee hours—a perfectly lovely place to sip and enjoy the view.


Insider Tip Indie art lovers will want to visit Portland on the first Friday of each month when the local galleries, studios, and Museum of Art are open free to the public from 5–8 p.m.

1 The holy grail of outdoor stores, the L.L. Bean flagship store could make a nature lover out of the most tried-and-true couch potato. And, it's open 24 hours. Make sure to browse the shops and outlets in the adorable surrounding town.

2 Head back into Portland to enjoy the working Waterfront District. The seaside area—Commercial Street, cobblestoned Fore Street, and brick-lined alleyways—is admittedly touristy, but there are some funky galleries sprinkled in. And you'll want to take some time to head up Exchange Street to the shops and galleries located toward Congress Street.

3 The name gives away the secret to its signature Belgian Fries, but Duckfat wants you to know why you can't get enough of its, well, duck-fat-fried Maine potatoes. The popular sandwich shops also serves up a sensational poutine. While the tight space may feel crowded, calm your nerves with local beer and wine.

4 Walk off lunch by meandering along Commercial Street to the Maine Narrow Gauge Railroad Museum. The 1.5-mile train ride gives the coastal view of the city, offering a short tour along the waterfront of Casco Bay.

5 What's a city without a good gourmet cupcake establishment? In Portland, baked goodies are on Fore Street at East End Cupcakes, where you can happily ruin your diet with vanilla, chocolate, lemon, peanut butter ... and bacon.

6 Some of the city's biggest dining buzz is over at Grace. The establishment has made a name for itself for its unique location—a restored church—and specialties including house made cavatelli, lobster stew, and hanger steak.


1 Grab your Parisian macarons and fresh-roasted coffee to-go at Mornings in Paris, then head down 295 toward Saco where Biddeford Pool hosts a stellar nature walk. The less-than-a-mile East Point Sanctuary Trail spans a short meadow before opening up to a grand vista of the rocky coastline and Wood Island Lighthouse.

2 Route 9 from Saco into Kennebunkport leads you to Ocean Drive, home to some of the area's most fabled scenery. The few miles of meandering coastline from roughly Marshall Point Road to Dock Square in Kennebunkport center takes in the grand mansions as well as the majestic site of the surf against the rocks. About halfway along, make sure to wave at the former president—known as Bush 41 in these parts—as you pass by the Walker's Point compound (you'll know it by the gatehouse at the entrance). Along the way, recharge with a burger and a great view at The Ramp.

3 Release your inner treasure hunter. Devout antiques enthusiasts will find paradise on Route 1 with dozens of dealers spanning the 30 miles between Arundel and Kittery. Look for the full range, everything from mom-and-pop shops to "super stores" like Arundel Antiques (1713 Portland Road; 207-985-7965). The perfect ending: a comfort-food meal at the ultra-kitschy Maine Diner.

Where to Stay

The hip Tides Beach Club (rooms from $225/night) hotel has the chic flair of nouveau hotel and the soul of a New England grand dame. There are just twenty-one rooms, all lovely, and the crisp lobby with overstuffed chairs stays lively well into the night.

Some bigger rooms at the classic and friendly MaineStay Inn and Cottages (rooms from $150/night) include kitchens, and all who stay more than one night receive beach parking passes. You also have the benefit of being just a few steps from town. Breakfast is included; guests in the cottages can have their morning meal delivered to their door. Families are welcome in the cottages.

The well-located Portland Regency Hotel & Spa (rooms from $149/night) sits on a block abutting Fore Street, just steps from the wharf and all the spoils of Portland's historic waterfront district.

When to Go

Beach lovers will find that many (but not all) beach shops and restaurants shutter after the prime May–October season. Whether Maine is a year-round destination depends largely on your desire and disposition. Portland and Freeport are dependable January-December city destinations (L.L. Bean is open almost all the time).

Hotel prices can change week-to-week, sometimes day-to-day, depending on occupancy and season. Memorial Day through Labor Day is your high season, when many hotels have two-night minimums. In the off-season, rooms can drop hundreds of dollars per night.

How to Get There

By Car: The Maine Coast, Portland, and Freeport areas are best accessed by car. The state line (around Kittery) is about sixty miles from Boston. Freeport is about twice that, at 120 miles. Driving the distance on summer weekends could take hours, as traffic can back up all the way to the New Hampshire border. Take I-95 to Wells or I-295 to Portland and Freeport.

Note that police are especially vigilant along roads connecting the highway to the coast where speed limits drop substantially. Beach access is typically open to anyone; the challenge is where to park. Many inns provide coveted parking passes to guests staying more than one night.

By Train: Amtrak offers trains several times daily between Boston and Portland, with midway stops including Saco and Wells, but you'll have to figure out how to get around once you arrive. Bicycles are a great way to navigate—bring your own or rent from one of many area shops.

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