The Best Road Trips in America

Highway 101 From San Diego to Seattle

Highway 101 From San Diego to Seattle
PHOTO: Jesse Wong
Highway 101 From San Diego to Seattle
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Highway 101 From San Diego to Seattle

Photo: Chuck Rolan/Shutterstock
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In the pages of Great American Road Trips, the drive from San Diego to Seattle should be at the very top.

At A Glance

STARTSan Diego, CaliforniaENDSan Diego, CaliforniaMILES
16 nightsstates
California, Oregon, Washington

The route, which glides along the coast from Southern California’s sunny beaches to Northern California’s redwoods, then on to rocky Oregon shores and the rainforests of Olympic National Park, is beyond beautiful. Along the way, the West Coast’s most dynamic cities, each one a worthy destination in-and-of-itself, line up like the pearls in a 2,878-mile long necklace. From its epic views to its incredible food, its hiking trails to its city streets, San Diego to Seattle 101 is the trip of a lifetime. ...Read More

Highway 101 From San Diego to Seattle
PHOTO: Jesse Wong

At A Glance

STARTSan Diego, CaliforniaENDSan Diego, CaliforniaMILES
16 nightsstates
California, Oregon, Washington

The Itinerary

San Diego to Los Angeles, California STOP 1  San Diego to Los Angeles
Los Angeles to San Luis Obispo, California STOP 2  Los Angeles to San Luis Obispo
San Luis Obispo to Big Sur, California STOP 3  San Luis Obispo to Big Sur
Big Sur to San Francisco, California STOP 4  Big Sur to San Francisco
San Francisco to Point Reyes National Seashore & Tomales Bay, California STOP 5  San Francisco to Tomales Bay
Tomales Bay to Mendocino, California STOP 6  Tomales Bay to Mendocino
Mendocino to Eureka, California STOP 7  Mendocino to Eureka
Eureka to Brookings, Oregon STOP 8  Eureka to Brookings
Brookings to Newport, Oregon STOP 9  Brookings to Newport
Newport to Astoria, Oregon STOP 10  Newport to Astoria
Astoria to Olympic National Park, Washington STOP 11  Astoria to Olympic National Park
Olympic National Park to Seattle, Washington STOP 12  Olympic National Park to Seattle
Seattle to Portland, Oregon STOP 13  Seattle to Portland
Portland to Ashland, Oregon STOP 14  Portland to Ashland
Ashland to Sacramento, California STOP 15  Ashland to Sacramento
Sacramento to San Diego, California STOP 16  Sacramento to San Diego

San Diego to Los Angeles, California

San Diego
2 h 40 m
125 mi
Los Angeles
Route: California-dream your way out of San Diego and along the Pacific Coast Highway (PCH). Pass through Orange County’s classic beach communities before heading slightly inland to the heart of Los Angeles.

Town: In Oceanside, take a walk along the wooden Oceanside Pier, one of the state’s longest, and catch a wave at South Carlsbad State Beach. Swing by the California Surf Museum for a look at the iconic Southern California sport and the legendary athletes who have made their mark.

Eat & Drink: Lunch on the “best pies in the West” at Betty’s Pie Whole Saloon in Encinitas. They’ve got a wide range of sweet and savory selections to eat there or on the road.

Nature: Get out on the water in Dana Point, post up at Doheny State Beach, or walk the trails at Dana Point Headlands Conservation Area to get a glimpse of the majestic mammals that frequent these waters. Whale watching tours depart from Dana Point Harbor.

Do: The options for things to do in Los Angeles are virtually endless. Wander through massive Griffith Park (don’t miss the historic Griffith Observatory) or stop by the La Brea Tar Pits for a glimpse of prehistoric Los Angeles. Some of the country’s best modern art is housed at the Los Angeles County Museum of Art (LACMA).

Eat & Drink: Dig into sisig and lumpia at the hip and modern Filipino restaurant Ma’am Sir or Middle Eastern specialties from beloved Chef Ori at Bavel. After dinner, The Slipper Clutch, a downtown bar inspired by New York punk rock, serves up highballs and craft beer with a side of pinball.

Stay: Los Angeles is huge and getting from one neighborhood to another can be a major time suck so choose your hotel’s location carefully. In Koreatown, between Hollywood and downtown, the boutique LINE LA boasts local art and regular events for around $250/night. Find art deco nostalgia with a contemporary edge in the casually sophisticated Mayfair Hotel downtown ($150/night).

Breakfast: Get a classic LA diner breakfast at the House of Breakfast or one inspired by LA’s cultural diversity at Koreatown’s Here’s Looking at You.


Los Angeles to San Luis Obispo, California

Los Angeles
3 h
189 mi
San Luis Obispo
Route: Navigate north up the PCH towards celebrity-hangout Santa Barbara. Outside the city you enter wine country and pass through Solvang, one of the West Coast’s quirkiest towns, before returning to the coast and San Luis Obispo.

Town: In Santa Barbara, see what’s blooming at the Santa Barbara Botanic Garden or visit the Old Mission, one of California’s original 18th century Spanish missions. There’s plenty of shopping to be done downtown where luxury retailers and boutique stores rub elbows with larger chains.

Eat & Drink: The longtime local favorite La Super-Rica Taqueria packs such authentic flavor that Michelin gave it a nod in its 2019 guide.

Nature: Sprawl out on the sand or take a swim at Arroyo Burro County Beach Park, called Hendry’s Beach by locals.

Roadside Attraction: The bizarre wine country town of Solvang is equal parts Danish village and Disney movie.

Do: There are vineyards galore just outside San Luis Obispo in the Edna Valley. Join an organized wine tour or plan your own with a wine-touring map available at the Old Edna Townsite. A historic Mission, the Mission San Luis Obispo de Tolosa, still stands in the downtown historic district.

Eat & Drink: The craft eatery Taste!, which serves everything from classic burgers to pork banh mi, has been winning best restaurant awards in SLO since it opened in 2014. At the Sidecar Cocktail Co., sip on artisanal margaritas and tiki drinks or go for dinner, when the brick-walled bar/restaurant serves some of the best comfort food in town.

Stay: The popular themed rooms at the world-famous Madonna Inn include everything from “Yosemite rock” to “Love Nest.” The kitschy on-site Silver Bar Cocktail Lounge is worth a pop in, whether you are staying here or not.

Breakfast: Over 100 different delectable donut flavors are available every day (including vegan and gluten-free options) at SloDoCo Donuts.


San Luis Obispo to Big Sur, California

San Luis Obispo
2 h 15 m
107 mi
Big Sur
Route: Head north past Cambria and toward the rocky bluffs, towering redwoods and rushing waterfalls of Big Sur, where the California coast puts on one of its most spectacular shows.

Town: The laid-back beach town of Cambria extends from beautiful Moonstone Beach to a quaint downtown peppered with antique and boutique shops. Swing by Nitt Witt Ridge, a homemade completely of garbage and a bastion of folk art, for a tour or a photo.

Eat & Drink: Get ultra-fresh seafood plucked straight from Morro Bay at The Galley, a waterfront restaurant on the Embarcadero.

Roadside Attraction: The lavish Hearst Castle, built for publishing magnate William Randolph Hearst by early 19th-century lady-architect-extraordinaire Julia Morgan, has more than 40 bedrooms, 61 bathrooms, indoor and outdoor swimming pools, a movie theater and 127 acres of gardens.

Photo Op: Snap some zebras. Zebras?! Yup, zebras. The descendants of those once kept at Hearst Castle are often visible from the side of Highway 1 in San Simeon.

Do: Get a look at Big Sur’s iconic McWay Falls from Highway 1, then hit the trail at Julia Pfeiffer Burns State Park or the water at Sand Dollar Beach or Andrew Molera State Park.

Eat & Drink: Nepenthe isn’t the cheapest spot in town but its location alone, crowning the top of a ridge overlooking the Pacific, is worth the splurge. Get a cocktail or enjoy a full dinner of steak and seafood out on the patio.

Stay: If you have the gear for a night under the stars, snag a campsite at Julia Pfeiffer Burns State Park ($30/night). To get a reservation, plan to book as far in advance as possible. The Big Sur Lodge is a clean, comfortable option for around $300/night but if you’ve got cash to burn, you won’t regret a night at the epic Post Ranch Inn (around $1,100/night).

Breakfast: The rustic-modern Big Sur Bakery has coffee, fresh-baked bread and pastries, and a selection of heartier breakfast options.


Big Sur to San Francisco, California

Big Sur
3 h
149 mi
San Francisco
Route: Travel on toward San Francisco. Past the artist colony of Carmel and the town of Monterey (the setting for John Steinbeck’s 1945 novel Cannery Row) stick to Highway 1 and the beach towns that line the coast of the Bay Area. This route adds 30 minutes to the trip but is a much more interesting drive than going up Highway 101.

Town: Tiny Carmel has long drawn artists with its charm. Explore the town’s galleries and boutiques and, if you have the time, take a quick detour down 17-mile drive for lovely views and a look at how the other half lives.

Eat & Drink: There’s always time for chowder! Stop at the roadside favorite Sam’s Chowder House in Half Moon Bay for a bowl and a beer on the patio.

Photo Op: Cross the world-famous Bixby Creek Bridge on the northern end of Big Sur then pull over to get the perfect shot.

Do: From the “Painted Ladies” (Victorian homes) of the Haight to the back-alleys of the largest Chinatown outside of Asia, San Francisco is one of the country’s most enchanting cities. The murals in the Mission neighborhood, North Beach’s Coit Tower, and downtown museums like the SFMoMa are among the many must-sees.

Eat & Drink: Get an authentic modern take on Chinese food at Mister Jiu’s or a San Francisco-style burrito from a city favorite, La Taqueria. After dinner, experience the dark side of tiki with artisan cocktails served in a doomed plane at Last Rites.

Stay: The ultra-stylish Proper Hotel near the Civic Center is a carefully orchestrated gallery of art and design with a popular rooftop bar starting at around $175/night. The boutique Hotel Kabuki in Japantown will swath you in its Zen aesthetic for around $325/night.

Breakfast: Before heading over the Golden Gate Bridge to Marin, grab a satisfying Southern breakfast in Lower Haight at Two Jacks Nik’s Place. Out near the beach, find Outerlands in the Outer Sunset, a beloved brunch spot with killer Dutch pancakes, or the Cliff House, an SF historical landmark overlooking Ocean Beach where the popovers are hot, free and endless.


San Francisco to Point Reyes National Seashore & Tomales Bay, California

San Francisco
1 h 40 m
50 mi
Tomales Bay
Route: It’s a short drive today over the Golden Gate Bridge and up Highway 1 to the Point Reyes National Seashore and the oyster-rich waters of Tomales Bay.

Town: The tiny, historic town of Point Reyes Station has a handful of pleasant shops and restaurants. It’s a lovely stop before hitting the wildlands of the national seashore a few miles down the road.

Eat & Drink: One of Northern California’s best cheese purveyors, Cowgirl Creamery calls Western Marin home. Pick up a round of Mt. Tam, the creamery’s flagship triple cream, along with bread, charcuterie and wine for lunch al fresco.

Photo Op: Cross the Golden Gate then pull over at the Golden Gate Bridge Vista Point for a view of the iconic architectural marvel in all its glory.

Detour: The “hidden” town of Bolinas, a small surfing community in a cove of Bolinas Bay, is about a 10-minute drive from Highway 1. The community abuts Mount Tamalpais and you can hike straight from town into the redwoods that sprout from Marin’s tallest mountain.

Do: The Point Reyes National Seashore is an unusual mix of historical ranching and dairy lands and protected wilderness. See the wild Tule Elk at Tomales Point, whale watch from the 150-year old Point Reyes Lighthouse and get a look at the elephant seal colony at Chimney Rock.

Eat & Drink: When you’ve had your fill of Point Reyes, hit the road to drive up the inland-side of Tomales Bay. The Marshall Store, a roadside joint with barbequed oysters, Dungeness crab sandwiches, and other delights from the bay is always worth a stop.

Stay: About a dozen miles up the road from The Marshall Store, Nick’s Cove has well-appointed cabins that hang out over the calm Tomales waters. Nick’s also has a fantastic farm-to-table restaurant (and their own hillside farm, The Croft), a historic boathouse for sipping artisan cocktails, and a small beach with a fire pit for roasting marshmallows after dark.

Breakfast: It’s a 10-mile drive to Valley Ford and the Estero Cafe, a local cafe with a knack for breakfast.


Tomales Bay to Mendocino, California

Tomales Bay
2 h 40 mi
129 mi
Route: It’s a day of spectacular views and quaint coastal towns as you continue up the PCH towards Mendocino.

Town: In Bodega Bay, tool around town on a bike or rent a kayak for a few hours on the water. Four miles from the coast is the village of Bodega, the filming location for Alfred Hitchcock’s 1963 film The Birds.

Eat & Drink: In Jenner, the Russian River meets the sea. Find stunning views of both at the intimate River’s End Restaurant which specializes in local seafood and seasonal produce.

Nature: In Point Arena, Bowling Ball Beach is littered with perfectly round boulders carefully carved by the waves.

Do: This laid-back town is a mecca for artists and gallery owners. Check out the Mendocino Art Center then browse some of the many galleries in town. If you prefer your art in liquid form, there are a number of wineries in nearby Anderson Valley.

Eat & Drink: Farm-to-table California cuisine is on the menu at the cozy Trillium Cafe. End the night with a shot and a beer at Dick’s Place, a dive on Main Street over a century old.

Stay: The Blue Door Inn is an elegant Victorian bed and breakfast with a modern aesthetic starting at $199/night. Many of the rooms have fireplaces, soaking tubs, and views of the Pacific.

Breakfast: Grab a coffee and breakfast (or just a pastry for the road) at the Goodlife Cafe & Bakery.


Mendocino to Eureka, California

3 h
143 mi
Route: Today’s route takes you away from the coast and into the weird and wonderful world of rural Northern California on the Redwood Highway (Hwy 101). At the day’s end, you’re back at the coast in Eureka, a city which rose to prominence during the Gold Rush Era.

Town: Leggett is crawling with unusual attractions just kitschy enough to be fun. Drive through a massive Sequoia at the Chandelier Drive-Through Tree, visit the World Famous Tree House, pop into the One Log House, and take home a sasquatch effigy at the Legend of Bigfoot Gift Shop.

Eat & Drink: Leggett’s roadside cafe, The Peg House, has a large patio, live music, and burgers and oysters hot off the grill.

Roadside Attraction: All of Leggett’s roadside attractions are amusing but Confusion Hill takes the cake. Built for mid-century roadtrippers, this mysterious spot is home to the “gravity house,” the “chipalope,” and the world’s tallest free-standing redwood chainsaw carving.

Detour: The well-maintained Victorian town of Ferndale is so charming that it has shown up in a number of movies and TV shows, including 1995’s Outbreak and 2001’s The Majestic. It’s also got a spectacular hillside cemetery as creepy as it is lovely. Find Ferndale a 10-mile drive towards the coast from Hwy 101.

Do: The entire town of Eureka has been named a historic landmark but the best-preserved blocks are located in Old Town. Explore the neighborhood on foot and don’t forget to check out the Carson Mansion, considered the grandest Victorian home in the US.

Eat & Drink: The sophisticated-yet-unstuffy Humboldt Bay Provisions deals in fresh local oysters and hand-crafted cheeses, meats, breads and desserts. For a more laid back meal, hit the Lost Coast Brewery Taproom, where they’ve got a menu full of sandwiches, salads and apps and some of the best beer in town.

Stay: Get your own slice of Victorian heaven with a night’s stay at the historic Carter House Inn. Rates start around $200/night.

Breakfast: Fill up on breakfast favorites like French toast, biscuits & gravy, and eggs benedict at The Green Lily Cafe.


Eureka to Brookings, Oregon

2 h 10 m
106 mi
Route: Bouncing back-and-forth from coast to forest, today’s drive takes you north through Redwoods National & State Parks and over the Oregon state border.

Town: Stop in at Crescent City to check out the beautiful Battery Point Lighthouse, one of the oldest on the West Coast. In town, you’ll find plenty of shops and galleries to peruse as well as cafes and restaurants.

Eat & Drink: Fill up on sandwiches, soup, and salad at the Log Cabin Diner in Klamath. After lunch, say hello to the emus that live next door.

Nature: Redwoods National & State Parks is a collection of protected spaces stretching almost 50 miles from Crescent City to Orick, California. Walk among the redwoods in Jedediah Smith Redwoods, visit lush Fern Canyon in Prairie Creek Redwoods, and watch the Roosevelt elk graze near Gold Bluffs Beach.

Do: The redwoods and coastal views don’t stop at the Oregon border. In Brookings, take a hike along the Oregon Redwoods Trail and admire the rock formations rising out of Lone Ranch Beach.

Eat & Drink: Indulge in super fresh sushi and seafood at local favorite, the Pacific Sushi & Grill. At the Oxenfre Public House, a gastropub serving local, fresh, organic food late into the night, you can also down a stiff drink and check out live music.

Stay: Wake up with a view of the Pacific at the Beachfront Inn, a comfortable and modern hotel with rooms starting around $190/night.

Breakfast: Get pancakes and other classic breakfast dishes at the rustic diner Mattie’s Pancake House.


Brookings to Newport, Oregon

4 h 15 m
205 mi
Route: The Oregon Coast pulls out all the stops today as you head north from Brookings, through the fishing town of Bandon, past the Oregon Dunes National Recreation Area and on to Newport.

Town: Once a major fishing hub on the Oregon Coast, Bandon now caters more to tourists with fun shops, harborside eats, and a cheese-producing creamery, Face Rock.

Eat & Drink: Nosh on award-winning fish tacos, Dungeness crab rolls, and local oysters at the no-frills Tony’s Crab Shack by the water in Bandon.

Photo Op: The rocky coastline in Cape Perpetua forms delightful natural fountains and churns at the Spouting Horn and Thor’s Well.

Do: See otters and fish endemic to this region of the Pacific at the Oregon Coast Aquarium or walk along the town’s historic bayfront where seafood processing has been ongoing for over 100 years. At the northern end of town, the Yaquina Head Lighthouse stands tall above Nye Beach’s long stretch of sand.

Eat & Drink: Splurge on a dinner of seafood prepared with unique international flavors at Local Ocean then head to the historic local dive, the Bay Haven Inn. Before going in, stop across the street to visit the colony of sea lions that post up at the harbor.

Stay: Let the sounds of the sea lull you to sleep at the Ocean House Bed & Breakfast at Nye Beach for around $250/night or The Whaler, a cozy motel with ocean views and a private balcony in every room ($115/night).

Breakfast: The hole-in-the-wall Cafe Stephanie serves an excellent daily breakfast menu with options like quiche, crepes and breakfast burritos.


Newport to Astoria, Oregon

3 h
133 mi
Route: Highway 101 sweeps inland today, passing through the outer edge of Tillamook State Forest before heading back to the coast and the site where Lewis and Clark first saw the Pacific. The day’s drive ends in Astoria, a port town and one of the stars of 1985’s The Goonies.

Town: Go for a stroll along Cannon Beach, a wide swath of golden sand punctuated by massive monoliths, including the 235-foot tall Haystack Rock.

Eat & Drink: Brake for some cheese (and a tour) at the Tillamook Creamery in Tillamook. The on-site cafe sells multiple styles of mac n’ cheese, as well as pizza, sandwiches and ice cream.

Do: Learn about Lewis and Clark’s epic adventure to discover the West in the early 19th century and peek inside their winter shelter, Fort Clatsop, at the Lewis & Clark National Historic Park. In town, Goonies fans will get a kick out of the Oregon Film Museum while aficionados of architecture and design will enjoy the Flavel House Museum.

Eat & Drink: Astoria’s food/drink scene is best known for its seafood and beer, both of which you can find tasty versions of at the Buoy Beer Company. But for something different, check out the traditional Eastern European dishes served at Drina Daisy Bosnian Restaurant.

Stay: Find modern elegance for a song at the boutique Hotel Elliot (around $115/night) or check in at the stylish Commodore Hotel, a historic property downtown for around $100/night.

Breakfast: Artisan breads and seasonal, organic breakfast dishes are made fresh daily at the worker’s collective, the Blue Scorcher Bakery & Cafe.


Astoria to Olympic National Park, Washington

2 h 45 m
132 mi
Olympic National Park
Route: It’s your last day along the coast so soak in the views as you cross the border into Washington state and head up to Lake Quinault in Olympic National Park.

Town: In the industrial harbor town of Aberdeen, you’ll find several homages to Kurt Cobain, who grew up here in the 70s and 80s. See memorials to the man above and below the bridge in Kurt Cobain Memorial Park and get a look at his childhood home at 1210 E. First St.

Eat & Drink: Have a pint alongside high-quality gastropub fare at the more than century-old 8th Street Ale House in Aberdeen.

Detour: It’s about a 15-minute drive from the fork in the road north of Gray’s Harbor City to Ocean Shores, a well-loved summer vacation spot with an endless beach.

Do: While you won’t be able to see the entirety of Olympic National Park, a place that covers more than a million acres of diverse landscape, you can explore its lower reaches. Head for Lake Quinault where you can swim, fish or boat in the lake or hike the Quinault Rain Forest Trail.

Eat & Drink: Dine on the delights of the Pacific Northwest at The Salmon House at the Rainforest Resort. Their menu includes house-smoked salmon, steak, pasta, and selections from their full bar.

Stay: A perfect remnant of mid-century Americana, the waterfront Lake Quinault Lodge has a wide lawn set with Adirondack chairs, outdoor games, and a swimming dock. Rates start around $200/night. Find camping nearby for $25/night at the Falls Creek Campground.

Breakfast: Grab breakfast with a view of the lake in the Lake Quinault Lodge’s Roosevelt Room.


Olympic National Park to Seattle, Washington

Olympic National Park
2 h 45 m
154 mi
Route: Backtrack to Aberdeen then head east through the state capital of Olympia and north on I-5 to the bustling city of Seattle.

Town: Make a stop in the state capital, Olympia, for a tour of the legislature and supreme court or check out the Monarch Sculpture Park and its many outdoor works of art. If you’re traveling with kids, they’ll get a kick out of the Hands On Children’s Museum.

Eat & Drink: Order an oh-so-satisfying sandwich or salad at the popular Lucky Lunchbox in Olympia.

Do: Whether it’s your first time in Seattle or your 100th, the city’s greatest hits—including the delicate sculptures at the Chihuly Garden & Glass Museum, the bustling seafood market Pike Place, and the iconic Space Needle—never get old. Options a little further off the beaten track include a visit to the Fremont Troll, the Science Fiction Museum and Hall of Fame, and Seattle Underground.

Eat & Drink: Seattle’s food scene is nothing short of fantastic. Find excellent Latin American and Cuban food at Mojito, masterful Indian at Pioneer Square’s Nirmal’s, and fresh seafood at Matt’s in the Market. Sip martinis and more at Bathtub Gin & Co., an unpretentious basement speakeasy in Belltown.

Stay: Get an affordable night’s stay (starting around $100/night) at the colorful, art accented Maxwell Hotel at the base of Queen Anne Hill. The Kimpton Alexis Hotel epitomizes the aesthetic of the PNW, with contemporary style and a palette of marine blues and forest greens (around $300/night).

Breakfast: Start the day off with a comforting spread from Fat’s Chicken and Waffles. On the weekends, the Vietnamese restaurant Monsoon prepares an extraordinary dim sum brunch.


Seattle to Portland, Oregon

3 h
174 mi
Route: Today’s drive is a fairly uneventful three hours straight down I-5 through the (mostly) urban corridor between Seattle and Portland.

Town: Seattle’s sister-city to the south, Tacoma boasts several interesting museums including the Tacoma Art Museum, the Washington State History Museum, America’s Car Museum and the cone-shaped Museum of Glass where you can also take a glass-blowing workshop.

Eat & Drink: In Tacoma, take a culinary ride through Southeast Asia with Indo Street Eatery’s interpretations of street food favorites like dumplings, satays, curries and noodles.

Do: Portland, the Emerald City, has plenty of parks and gardens to admire, including the serenely beautiful Portland Japanese Garden. Walk the streets of Old Town (don’t forget to stop in at nearby Powell’s Books) and take in the work at the Portland Art Museum. About 45 minutes south of the city is Willamette Valley and some of the best vineyards and wineries on the West Coast.

Eat & Drink: Both PDX’s restaurant and food truck scenes are unbeatable. Dine on pierogies and potato pancakes at the sophisticated Polish restaurant Delores or get in line for hearty plates of soul food at the popular Kee’s #Loaded Kitchen. After dinner, sip cocktails at the horseshoe bar at adorable Angel Face in Northeast Portland.

Stay: Fashioned out of a historic elementary school, McMenamins Kennedy School Hotel is one of Portland’s most unique with 57 rooms (some still hung with the chalkboards of yesteryear), multiple bars, a movie theater, a brewery and a soaking pool for around $140/night. A more luxurious stay awaits at the boutique Hotel Eastlund, a fun and modern property with a rooftop bar and restaurant (starting around $200/night).

Breakfast: In the morning, sit down for a meal at the downtown French “pastry luncheonette”, Maurice or pick up a breakfast sandwich at the Fried Egg I’m In Love food cart in Pioneer Courthouse Square.


Portland to Ashland, Oregon

4 h 30 mi
284 mi
Route: Ride through the agricultural lands of central Oregon and into the foothills of the Cascade Range and the Siskiyou Mountains to Ashland, a small town famous for its annual Shakespeare Festival.

Town: Eugene is home to the University of Oregon which means that, despite this city’s relatively remote location, there’s more to do than you might expect. Check out one of the area’s many wineries and breweries, hike down the McKenzie River National Recreation Trail, or catch a show at the Hult Center for the Performing Arts.

Eat & Drink: Fill up on authentic, home-style Mexican at Eugene’s 1960 Cocina.

Do: Ashland is best known as the home of the Oregon Shakespeare Festival, which stages performances throughout much of the year. If you’re visiting in winter, check out the Mt. Ashland Ski Area. During warmer months, the mountain opens its trails to bikers and hikers.

Eat & Drink: With a menu influenced by Japanese omakase and PNW flavors, MAS is one of the best restaurants in Ashland. For something less pricey, check out Brothers’ Restaurant, a downtown institution famous for deli staples like lox and bagels, corned beef hash, and chicken soup. Fill up on local and regional craft beer at The Growler Guys.

Stay: The Peerless Hotel, a boutique bed and breakfast in Ashland’s Historic Railroad District, is dripping with Victorian charm. Rates start around $120/night.

Breakfast: Have breakfast at the cheery Morning Glory Cafe, which has a lovely back garden for lingering over your meal.


Ashland to Sacramento, California

5 h
294 mi
Route: It’s an eye-popping route through the mountains and down into Northern California where views of Mount Shasta will dominate your drive almost all the way to Sacramento, the California state capital.

Town: Redding is a pleasant town on the shores of the Sacramento River. Learn about its history at the Shasta State Historic Park then stop by the Sundial Bridge, part pedestrian walkway, part art installation.

Eat & Drink: Nosh on chicken and waffle sandwiches, wings and tenders at Redding’s Chicken Shack.

Nature: Conquer magnificent Mount Shasta or go for a hike on some of the volcano’s more moderate trails.

Do: Pass through the early days of California’s Gold Rush-era in Old Sacramento then step further back in time at Sutter’s Fort, a major center of agriculture and trade during pioneer days. The civic-minded will appreciate a tour of the California State Capitol Museum and its surrounding gardens.

Eat & Drink: Get messy with pulled pork sandwiches, brisket and beer at the Urban Roots Brewery & Smokehouse or keep things Prohibition-inspired at the Shady Lady Saloon, which has a full menu that includes sandwiches and small plates.

Stay: The classy Kimpton Sawyer Hotel in downtown Sacramento is an urban retreat with an elevated pool deck and chicly-styled rooms starting around $175/night.

Breakfast: The breakfast and brunch staple Pushkin’s Kitchen serves classic egg dishes and bowls inspired by global cuisine.


Sacramento to San Diego, California

7 h 45 m
504 m
San Diego
Route: Today’s drive is long and, frankly, pretty monotonous. Steel yourself for at least eight hours through so-flat-it’s-sinking Central California and L.A. traffic before rolling into San Diego at the end of the road.

Town: If you are looking to break up the drive, Stockton is a decent enough stop in the virtual desert of agricultural lands at California’s heart. There’s a nice children’s museum here, as well as the Haggin Museum, an under-the-radar treasure trove of art and history.

Eat & Drink: Considered one of the tastiest restaurants on this lonely stretch of I-5, Willow Ranch in Buttonwillow serves mesquite barbeque, home-style favorites, burgers, and more.

Do: Whether you’re traveling in winter or summer, chances are San Diego will welcome you with lovely weather. Spend your visit at Balboa Park, San Diego’s large urban park and cultural center, or on the beach at La Jolla. After dark, hit the nightlife and events district, the Gaslamp Quarter,

Eat & Drink: Get some of the best tacos in town at Galaxy Taco or Italian American favorites at the neighborhood eatery, Cardellino. At the brewery/gastropub Amplified Kitchen & Beer Garden, sip an award-winning brew with a side of doner fries.

Stay: Treat yourself to the full beach resort experience at the San Diego Mission Bay Resort for around $325/night or bed down in the Gaslamp Quarter at the Hotel Indigo for around $175/night.

Breakfast: Wake up to North African-Baja fusion cuisine at Medina Kitchen or indulge in expletive-worthy food at Breakfast Bitch.


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