Shopping Weekend Getaway in Portland, Maine

Friday

1. The brews flow from 11:30 am to 1 am at Federal Jack's, a restaurant and brew pub on Maine's proud Beer Trail (see all 25 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, no tank tops. And 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.

Saturday

1. Get an early start to beat the shopping crowds. Drive into Freeport where a stellar breakfast—pancakes, waffles, French toast, breakfast burritos—awaits at the Fresh Batch.

2. 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.

3. 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.

4. The bicycles parked outside of The Farmer's Table tell you everything you need to know about this fresh-food establishment. Enjoy a hearty lunch of locally sourced and reasonably priced "Mediterranean Comfort Foods."

5. Walk off lunch by meandering along Commercial Street to the Maine Narrow Gauge Railroad Museum. The 1-1/2-mile train ride gives the coastal view of the city, offering a short tour along the waterfront of Casco Bay.

6. 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.

7. Some of the city's biggest dining buzz is over at Grace. Opened in 2009, 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.

Sunday

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 or, when exiting Kennebunk, with a cup of coffee and pastry at the Chase Hill Bakery.

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. The perfect ending: a comfort-food meal at the ultra-kitschy Maine Diner.