Astoria
Gateway to the Columbia

The tour of Astoria's Shallon Winery is pretty standard. Owner Paul Van der Velt discusses the pumps and fermenting tanks, then allows guests a peek into the laboratory where he fine-tunes the libations that bear the Shallon label. As you settle in at the tasting room's bar, though, you begin to get a sense of something not quite right. Maybe it's the large harp sitting in the middle of the winemaking equipment. Or the pinkness of the place—the color is everywhere, infusing the winery with a strange, valentiney glow. Or maybe it's the point where Van der Velt carefully pours you two glasses of his favorite creations: lemon meringue and orange chocolate wines.

With its maritime history and postcard Victorians, this seaside town is making waves.

Welcome to Astoria, a town that does things a little differently. Unlike its generic, sand-and-tan neighbors, Seaside and Cannon Beach, Astoria (the oldest U.S. settlement west of the Rockies) is a town with both history and color unmatched on the Oregon coast.

Perched on a gentle slope above the mouth of the Columbia River just below Washington state, Astoria radiates a Northern Exposure-esque charm. As you walk the shady streets, though, keep in mind that it wasn't always so peaceful. Known as "the wettest town in the West," Astoria once rivaled San Francisco for its cornucopia of gambling dens and bordellos. In 1896, it was the state's second-largest city and home to over 40 saloons. Despite the best efforts of reform-minded legislators (who outlawed "whooping" within town at one point), Astoria didn't quiet down until the entire state went dry in 1916.

Interacting with Astoria's colorful history is one of the biggest joys of visiting. Plan on coming in June when the Scandinavian Midsummer Festival turns the town upside down. This three-day party celebrates the waves of Finns, Norwegians, and Swedes who made up more than a quarter of the town's population in 1900. The weekend includes a parade, dancing, and a rollicking beer garden perfect for downing lutefisk and letting fly with a hearty Uff-da!

Even if you can't make the festival, there are plenty of fun ways to get in touch with Astoria's history.

Your first opportunity will likely come when you reserve a room. Astoria's fondness for its past is reflected in the number of Victorians transformed into bed-and-breakfasts.

One of your best bets is Clementine's. Owner Judith Taylor's selection of cozy, balconied rooms is complemented by two separate family-friendly apartments (one of which spent its early life as Astoria's Moose Lodge). Those looking to get away from the crowds should head for the Astoria Inn. Located a five-minute drive from downtown, the landmark's rooms are among Astoria's most romantic. Larger and no less historic, the Rosebriar Hotel was a convent before it was turned into a B&B-style hotel. Rooms range from simple to lavish, with those on the upper end featuring river views, fireplaces, and spas.

The remains of the Peter Iredale, buried on the beach at Fort Stevens State Park

Start your exploration of Astoria at the town's crown jewel—the Flavel House. Bar pilot George Flavel was a Donald Trump figure in Astoria's boomtown days; it was here in cupolaed splendor that he spent his retirement. The house is now a museum dedicated to Flavel.

Learn more about the town's bawdy era at the Heritage Museum (the "Virtue and Vice" exhibit is a frolicsome introduction to the town's lively past).

For a complete education on the local shipping trade and nautical exploration, head to the Columbia River Maritime Museum. Along with viewing a host of exhibits, visitors may peer through a working periscope and stroll the bridge of a World War II warship.

If tales of hardtack and scurvy have you hungering for some fresh grub, you're in the right place. The tiny Columbian Café is revered by foodies up and down the Oregon coast for its creative, fresh-off-the-boat dishes. Those with cast-iron stomachs should try the Too Damn Hot shrimp, while those with sensitive (read: normal) stomachs can stick to less searing dishes such as smoked salmon hash and curry broccoli crepes. At Someplace Else, another Astoria gem, owner and chef Lauren Arena takes frequent working holidays to learn cooking secrets from around the world; she complements her Italian standards with forays into French, Mexican, and Indian cuisine.

Work off your meal with some window-shopping. Finn Ware sells a smorgasbord of Scandinavian goods, from imported crystal to sauna supplies. The RiverSea Gallery is the best place to view the work of painters, potters, and other local artists.

Adventurous-types should take a drive south to Fort Clatsop National Memorial. Lewis and Clark (and an entourage that included Shoshone guide Sacagawea) spent an awful winter here in 1805-6. Having arrived at the height of the rainy season, the group hastily built a minuscule fort and hunkered down for four months of fleas and rancid elk meat. The reconstructed fort commemorates the explorers with films, exhibits, and reenactments of daily life.

To the north, there's Fort Stevens State Park. During World War II, a Japanese submarine fired at Fort Stevens, earning it the distinction of being the first military installation in the continental United States to be fired on by a foreign power since the War of 1812. Visitors can explore the labyrinth of concrete battlements, visit the military museum, or wander around the iron skeleton of the Peter Iredale, a freighter that ran aground in 1906.

Make sure you're back in time for sunset. On clear evenings, locals make a migration to the 125-foot-high Astoria Column. Covered in sepia friezes depicting the settlement of the West, the landmark sits on the highest point for miles around. As the last embers of the day wink out, all eyes gaze out over the same intersection of river and sea that has drawn explorers here for almost two centuries.