Seaside is the most earnest beach town in Oregon. With a beachfront promenade stretching a mile and half, a real Tilt-A-Whirl and the closest thing Oregon has to a boardwalk, it makes you nostalgic for golden days you never experienced—those South Carolina beaches from Nicholas Sparks novels, or where “literally so much drama” unfolded in Season 1 of Laguna Beach: The Real Orange County.

Seaside is just an hour and a half from Portland, so it's been the standard-issue getaway for local kids forever. And, unlike Portland, Seaside has barely changed at all in the past two decades. It's still full of small shops selling kites, Roxy board shorts and trashy T-shirts. Where else can you ride a surrey while eating a giant caramel apple and proudly wearing neon-green sweatpants that say "Seaside" down the leg?

(Henry Cromett)
(Henry Cromett)

Seaside's cheesiness is its charm. If you're here, don't fight it—go native and get the taffy, ride the creaky bumper cars and feed seals at the aquarium.

When you want a break from that vibe, there’s nearby Gearhart, Seaside’s own West Hills, where the beaches are nearly private and the houses are owned by wealthy Portlanders.

FRIDAY NIGHT

Get grocery-store drunk and stock up on party supplies

OK, you've made it to Seaside. Now, go straight to Gearhart. Do not stop at the Safeway for beer or Chinese food. Instead, spend the extra seven minutes to get to where the tiny yet bougie Gearhart Crossing Pub (599 Pacific Way, Gearhart, 503-738-7312, gearhartcrossing.com) sits in the middle of a small neighborhood store and deli, the kind of family shop where your summer-vacation crush bags groceries.

(Sophia June)
(Sophia June)

It's stocked with campfire supplies and Portland treats you might already miss, like Hot Lips sodas and kombucha. The in-store pub very recently started serving up pan-fried Willapa Bay oysters ($12 for six) and 14 beers. It also offers other snacks, like upscale nachos, oyster sliders and deviled eggs, plus it recently added eight sandwiches, six burgers and a kids' menu, turning this grocery store into a Seaside/Gearhart must-stop. Portland has arrived, but only Clatsop County locals get 10 percent off on Mondays.

Keep the party going

There are only three bars in downtown Seaside. They're all dives, but Dundee's (414 Broadway St., Seaside, 503-738-7006, dundeesseaside.com) is where the party's at, right on the boardwalk and just three blocks from the beach, with a giant sign in cowboy font and greasy wooden high tables.

(Sophia June)
(Sophia June)

Tourists and locals watch basketball games on the bar's 18 screens; play lottery games, darts, pool and shuffleboard while drinking plenty of Miller Light, Breakside IPA and Cannon Beach's Public Coast Red Ale from the bar's 18 taps; and scarf down pizzas.

Take a moonlit walk on the beach

(Henry Cromett)
(Henry Cromett)

On any clear night (and plenty of non-clear nights), the beach in Seaside turns into a campground, as dozens of campfires dot the sand. Look behind  you and you'll see a skyline of massive hotels—for a split second, you could be in Barcelona. Dip your toes in and then run back to the boardwalk—or, zip up your jacket and start finding a place to set up your own bonfire. S'mores are welcome, and alcoholic beverages are allowed—it's legal to drink on the beach here, so long as your chosen beverage is under 14 percent ABV. When you walk back, you'll notice that the Christmas lights are still up on the houses, but somehow it's just…nice.

(Sophia June)
(Sophia June)

SATURDAY MORNING

Breakfast at Riley's

The motto at this no-frills diner is "Where the locals go," and it sure seems to be true. Just a few blocks away from the hordes descending on downtown's Pig N Pancake, you'll find the same selection of slightly rubbery omelettes and watery coffee at Riley's (1104 S Holladay Drive, Seaside, 503-738-9701), but without the lines. Slide right into an open booth and keep the chatter down, lest you annoy the men trying to read their Daily Astorian in peace.

Fuel up with extra java

If there's any place that would unironically refer to coffee as "java," it's the Seaside Coffee House (5 N Holladay Drive, Seaside 503-717-0111, seasidecoffeeroasters.com). This shop is straight out of a college town circa 1992. Everything is a woody brown and it's filled with Seaside locals with laptops, roast their own coffee, have a nice tea selection and offers succulents for sale.

Go kayaking

(Henry Cromett)
(Henry Cromett)

One of Seaside's best features—and the thing that most distinguishes it from coastal towns built around deep-water bays—is the Necanicum Estuary, where you can go crabbing, bird watching and kayaking. The Seaside Lodge & International Hostel (930 N Holladay Drive, 503-738-7911, seasidehostel.net) rents kayaks—it's $25 for two hours, with life jackets and whistles included. Everyone at Seaside Lodge & International Hostel treats you like you're at a four-star hotel. You don't do any of the labor; they bring the kayak down for you, hand you paddles and drag the kayak back up a carpeted boat ramp afterward. On the journey, you might see an otter or even an eagle. The estuary is long and the current is fast (you'll be exhausted after paddling back up it), so getting out is easy—just avoid the crab nets as you paddle under the 12th Street bridge. You feel like you're in the middle of an easily navigable river, but with the smell of the ocean.

SATURDAY AFTERNOON

Fuel up for the rest of the day

(Henry Cromett)
(Henry Cromett)
(Henry Cromett)
(Henry Cromett)

Seaside may not be a port town, but it knows some fishermen. Buoy's Best Restaurant (1800 S Roosevelt Drive, 503-738-2722, bellbuoyofseaside.com) has the finest, freshest seafood in town, which comes on styrofoam straight from the Bell Buoy fish market next door. The shop is one of the only places approved to clean and sell razor clams, which means most restaurants up and down the coast are buying from them. Cut out the middleman and get the clam chowder, which made a respectable showing last year in our survey of notable chowders on the coast. It's rich and buttery thanks to an overnight marinade. Also, be sure to grab oyster shooters ($3) and breaded cod with waffle fries ($10).

Feed the animals

(Sophia June)
(Sophia June)
(Sophia June)
(Sophia June)

You go to Seaside Aquarium (200 N Prom, 503-738-6211, seasideaquarium.com) for the seals. This is possibly the jankiest aquarium you've ever been to, but it's also maybe the best $8 you can spend on the entire coast. Pay an extra $2 and you get fish to throw at the seals, who bark and whimper and slap their big bellies as they leap up to catch their dinner. Avoid the splash zone if you brought a nice camera; the seals whack their flippers on the water and soak you. Once you're past the seals, it's basically a room full of fish tanks, which doesn't look much more impressive than a pet store, with the exception of the open ones where you get to touch starfish and sea anemones. The aquarium opened in 1937, making it one of the oldest on the West Coast. In 1994, it got considerable attention when a drunken man stole the supposed largest lobster in the world from the aquarium. Now its carcass and a display of news clippings from the incident.

Drink with a view

There are no nice bars in Seaside. The regular bars are divey and the dive bars are very, very divey. Skip the other dive bar and head to The Bridge Tender (554 Broadway St., 503-738-8002), where it doesn't feel like a fight could break out. From the outside, it looks like SpongeBob's favorite dive bar, constructed with what looks like driftwood and without a single window on the façade. Once you're inside, there's a gorgeous view of the estuary. You can drink Buoy Pilsner while watching families on pedal boats shaped like swans.

Get a little fancy

Gearhart is notable for being the hometown of proto-foodie James Beard, namesake of the Grammys of food. So spend a little extra money on dinner at Pacific Way Cafe (601 Pacific Way, Gearhart, 503-738-0245, pacificwaybakerycafe.com). You'll find pinot grigio from the valley along with linguine in white clam sauce ($23.95, includes salad), which is decadent and packed tight with steamers and chopped ocean clams. Split it and pair it with the Willapa Bay oysters, breaded and grilled and served with cocktail sauce and fennel slaw. Pacific Way also makes cioppino ($29.95), the famous Italian influenced seafood soup of San Francisco that's lately been popping up around Portland.

Sip on espresso in a pastry cafe

Wake up early and drive back to Gearhart to get pastries from Pacific Way Bakery (601 Pacific Way, Gearhart, 503-738-0245, pacificwaybakery-cafe.com), which is attached to the cafe where you had dinner.

(Sophia June)
(Sophia June)

The tiny bakery makes goodies that are delicate and decadent, and sells out quickly. Order at the tiny counter and sit at a tiny circular marble table. You'll feel like you're in Europe as you nom on a raisin snail ($3.30) or a mixed fruit danish ($3.40) and sip on espresso.

Walk "The Prom"

The Seaside Promenade dates back to the 1920s, and there's something that feels distinctly East Coast about it, like a relic from the Jersey shore. It takes about 40 minutes to walk round-trip, which is the perfect amount of time to eat an ice cream cone and half a bag of taffy.

Amuse yourself

Long ago, I'd like to think Seaside was a bustling boardwalk. The only reason I think this is because of the mini-golf, bumper cars and Tilt-A-Whirl (Interstate Amusement Co., 110 Broadway St., Seaside, 503-738-5540), which have been on the Seaside boardwalk, in the middle of downtown, for 60 years.

(Henry Cromett)
(Henry Cromett)

It's cash-only and everything is even older and squeakier than Oaks Park. You'll get lost in the nostalgia of it all, suddenly finding yourself wanting a sweater set and a boyfriend who's getting drafted as you scarf down a Pronto Pup corn dog.

(Henry Cromett)
(Henry Cromett)
(Henry Cromett)
(Henry Cromett)

Stock up on sweets

It's not a cheesy family beach trip until you've wandered through a stocked candy store before having an existential crisis over whether to buy fresh fudge or saltwater taffy. When you're at the coast, get 'em both. First walk a block to Schwietert's Cones & Candy (406-A Broadway St., 503-717-8808, schwieterts.com) for a gooey caramel apple and the store's extensive Pez collection.

The taffy is tasty, but there's better around the corner at The Seaside Candyman (21 N Columbia St., No. 105, 738-5280, seasidecandyman.com), the oldest candy company in the town.

(Henry Cromett)
(Henry Cromett)
(Henry Cromett)
(Henry Cromett)

Here, you can spin a giant wheel and win some free taffy or popcorn. Even if you lose, you get free taffy. With a rainbow-tiled floor and 180 huge troughs, Seaside Candyman feels like a tiny beach-town take on Willy Wonka's Chocolate Factory.

Buy one of those neon Seaside sweatshirts

You can't leave Seaside without getting a highlighter-neon sweatshirt that says "SEASIDE," with an off-brand Hollister seagull logo. The venue in which to buy this is The Freedom Shop (111 Broadway, Suite 16, 503-738-4175,
thefreedomshop.com) on Seaside's Boardwalk. Rock it unironically.

WHERE TO STAY

Cheap

You can get a room at the Seaside Motel 6 (2369 S Roosevelt Drive, 503-738-6269, motel6.com) for around $70. There's no pool, you'll have to remember to bring your own shampoo and it's about a seven-minute drive from downtown Seaside. But as far as last-minute beach hotels go, you'll save a bunch. Haters may suggest you "bring your own sheets." This is overly alarmist, but you may do well to bring a fluffy pillow. It's not nice, but it's…fine.

Bougie

The Ashore Hotel (125 Oceanway St., 503-568-7506, ashorehotel.com) is
Seaside's version of the hipstery Ace Hotel. The town's chicest spot has a heated mineral soaking pool, a sauna and a fire pit lined with oyster shells. The floors are stone and the rooms are full of minimalist light fixtures with exposed lightbulbs. The small lobby bar serves Underwood wine and coastal craft beer in Mason jars and offers charcuterie plates with Olympia Provisions sausage and popcorn with coconut oil and salt.

(Henry Cromett)
(Henry Cromett)
(Henry Cromett)
(Henry Cromett)

You can stay in a queen room for around $220 a night, which includes a daybed and trundle bed, easily fitting a family of four. If you're looking to stay longer, many rooms are discounted for a two-night stay. The Ashore also has two-room suites, which sleep four, for around $290.

(Henry Cromett)
(Henry Cromett)
(Henry Cromett)
(Henry Cromett)

Related: