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21 Towns Like Ashland, Oregon

If you enjoyed the rich history, small town vibe and the close relationship of Ashland, Oregon with the surrounding nature, here are several other towns with the same flair.

This is an aerial view of Ashland, Oregon surrounded by trees and mountain.

Nestled inside the state of Oregon is a college town called Ashland, Oregon. The picturesque small town is full of Victorian architecture, hipsters, hippies, yuppies, hikers, skiers, artists, craft beer, bookstores, and its famous Shakespeare Festival. Its laid-back liberal arts vibe is hard to replicate, but there are places out there that do have a bit of Ashland flavor.

Towns like Ashland, Oregon, have a love of the arts and the outdoors. Port Townsend, Washington, is one of its closest sisters. But other places such as Missoula, Montana, Burlington Vermont, La Crosse, Wisconsin, and Sun Valley, Idaho have similarities to Ashland, too.

Ashland isn’t a terribly big place, with only a little over 21,000 people. But they have museums, famous Lithia Water from their natural springs (it tastes disgusting), the Ashland Watershed Trail System, and the Siskiyou Mountains. Hard to beat. But we’ve found 21 towns that possess a touch of that Ashland spark.

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21 Towns Similar to Ashland, Oregon

It is wise to understand what you hope to find when looking for a town like Ashland, Oregon. Is it the green trees and the mountains? Did you fall in love with the small town old-timey architecture? Do you love college towns and liberal politics? Are you into craft beer? Whatever it is you adore, you’ll find it in one of our 21 suggestions.

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Ann Arbor, Michigan

This is an aerial view of Ann Arbor, Michigan.

Ann Arbor, Michigan, is a university town situated on the lower peninsula of southeast Michigan. Like Ashland, Ann Arbor has a fiercely liberal vibe which allows their arts to flourish. The picturesque and walkable downtown is brimming with museums, art galleries, theater, and home to independent Literati Bookstore, a literary lovers paradise.

Those that love fresh food will be in heaven in Ann Arbor’s year-round farmers’ markets. If that’s not enough, Washtenaw County, where Ann Arbor resides, boasts fourteen of them. The town is brimming with culinary delights, from coffee shops, team rooms, Spanish tapas, the Tea Haus that sells loose tea by weight, and the famous Zingerman’s.

For outdoor enthusiasts, the area is full of trails and parks that cater to hikers, skateboarders, runners, and mountain bikers. Huron River is excellent for water sports. Come winter, folks enjoy ice skating, snowshoeing, and cross-country skiing. There is plenty of golf and fishing to do, too. The only thing missing is the mountains, but this area is far from flat.

Asheville, North Carolina

This is an aerial view of Asheville, North Carolina.

Asheville, North Carolina, is an eclectic mountain city with over twenty craft breweries and overflows with artists, including glass blowers, painters, and potters.  Essentially, it is the Appalachian version of Ashland, with a bohemian vibe giving a Southern touch complete with spicy apple butter.

They are a town of festivals, including the annual Mountain Dance and Folk FestivalAsheville Vegan Fest, Shindig On the Green, Miss Gay Latina, and North Carolina Ceramic Arts Festival. Another year around entertainment delights include magic acts by The Vanishing Wheelchair, numerous theater and stage companies, and live music at taverns, music halls, and nightclubs.

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The Blue Ridge Parkway, the popular scenic highway, runs right through the town. It’s unsurprising, given the area is surrounded by 3240,000 hectares of wilderness. People enjoy hiking and mountain biking through the area, enjoying the waterfalls, whitewater rafting, and taking a ride on the zip lines.

But even those that wander the town of 10,000 people will enjoy the leafy streets and their unique architectural mix, including Victorian, Arts and Crafts, Art Deco, Biltmore Style, and Modern design. It’s an urban landscape that welcomes nature.

Burlington, Vermont

This is a close look at church street in Burlington, Vermont.

Burlington, Vermont, is billed as Vermont’s largest city, but with a population of only 42,000, it retains the feel of a town. Home to the woke ice cream company Ben & Jerry’s, Burlington shares a similar political vibe and outlook to Ashland. Downton Burlington is also saturated in history and charm, with its brick-paved pedestrian mall, fountains, and tree-lined streets.

The area boasts plenty of local breweries, including Zero Gravity with both a restaurant and 30-barrel brewhouse and the progressive Switchback that is 100-percent employee-owned.  But the wealth of beer doesn’t begin to compare with its literary wealth of 24 independent bookstores.

Burlington brims with culture, hosting a wide range of live music events, including the annual Burlington Jazz Festival. Foodies will love Vermont Restaurant Week, Burlington Wine & Food Festival, Vermont Brewers Festival, and for the truly adventurous, the outdoor winter Ice Bar that celebrates local artisans along with the area’s acclaimed cuisine and drinks.

Burlington is a city for people that embrace the outdoors. In the summer, folks go camping, hiking, biking, and participating in various water sports. People camp and hike in winter, too, along with skiing, ice climbing, and snowmobiling. A lot like Ashland, actually.

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Bozeman, Montana

This is an aerial view of Bozeman, Montana with trees and mountains.

Bozeman, Montana, is a small city of over 46,000 folks and sits in the southern part of the state in the Rocky Mountains. Like Ashland, it’s a college town and bends liberal. The city is an attractive brick and Western with an abundance of greenery with a towering mountain backdrop.

The area is an eclectic mix of outdoor stores, coffee shops, and has a thriving artist community. There are many local breweries; the first to set up was Bozeman Brewing Company in 2001, and the relative newcomer is Nordic Brew Works. Bozeman is also home to the state’s largest independent book store, Country Bookshelf.

Bozeman hosts many festivals, including the Sweet Pea Festival, a three-day celebration of the arts. They have music and film festivals, rodeos, fairs, and farmers’ markets too. They are also home to the Museum of the Rockies, a Smithsonian affiliate famous for its dinosaur bone collection.

Bozeman is an outdoor paradise, be it skiing in the winter or rafting in the summer. Whether you want to camp, hunt, rock climb, or visit hot springs, Bozeman either has it, or it is right next door. After all, if the 80 miles to Yellowstone is too far to your taste, they have plenty of other parks to choose from.

Cambridge, Massachusetts

This is a close look at the Charles River in Cambridge, Massachusetts.

Cambridge, Massachusetts, is more than being home to MIT and Harvard University. The classic New England town has a population of 116,600 is full of historic sites, bookstores and literary wealth, craft breweries, and coffee houses galore.

Museum-lovers will enjoy the interactive exhibits at the  MIT Museum, the eclectic art collections at the Fogg Museum, and become emerged in the Harvard Natural History Museum.  

Festival lovers will adore the Harvard Square Chocolate Festival. But you might also delight in the Sheepshearing Festival,  The Italian Feast of Saints Cosmas & Damian, the Cambridge Science Festival, and more.

While enjoying the Comedy Studio, theaters, and fine dining, there are some unusual and endearing sites to hunt down. Take a peek at Pooh’s House, be dazzled by the vibrant colors at the Forbes Pigment Collection, and have an admiring snort over the O’Reilly Spite House, one of five New England Homes built out of, well, spite.

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Carmel-by-the Sea, California

This is a view from the sea of Carmel-by-the Sea, California.

Carmel-by-the Sea, California, is Ashland’s wealthier cousin. The picturesque town only has 4,000 residents, but it is popular with visitors, swelling up on the weekends. There is wine tasting, fine dining, and many wellness centers, spas, and fitness studios. The lauded beaches are popular with joggers, strollers, dog lovers, and surfers.

Book lovers will be enchanted by Pilgrim’s Way Community Bookstore & Secret Garden. The area has a thriving artist community, many galleries, and hosts an annual Bach Festival. There are also special guided tours that take you through the town’s hidden courtyards, secret pathways, and stunning gardens.  

Durango, Colorado

This is an aerial view of Durango, Colorado during fall.

Durango, Colorado, is a college town of 18,500 folks. It is nestled in a valley of the Rocky Mountains, right near the New Mexico border. Like most places on this list, it is an outdoor lover’s dream. Residents and visitors have a pick of places to ski in the winter. Come summer, and the biggest problem is choosing what you want to do.

The town is full of museums, restaurants, coffee shops, at least five brewpubs, and many independent book stores, including Maria’s Bookshop. Visitors love the hot springs, hot air ballooning, and the abundance of arts. But the most well-known attraction is the Durango & Silverton Narrow Gauge Railroad. It’s a brilliant way to take in the local scenery.

Eugene, Oregon

This is an aerial view of Eugene, Oregon during dusk.

Eugene, Oregon is for people who find Ashland too small, not woke enough, and want their local college to have a good football team (Go Ducks!). While the city has over 168,000 people, it retains a small-town feel.  Eugene is all about organic farmers, the arts, alternative living, marijuana, and tie-dye.

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After spending a day hiking in the diverse nearby landscape of wetlands, prairie, and two mountain ranges, you can attend a show by the well-respected Eugene Ballet Company. Or you can listen to an author discuss their book or catch some live music at Tsunami Books.  

The town is surrounded by local winemakers, host many museums, fairs, and shows at the Hult Center for the Performing Arts. Eugene and the surrounding area also host to many festivals, including the Eugene Scottish Festival, or indulge in Æbleskiver (delicious round Dutch pancake) at the famous Scandinavian Festival & Culture.

Harper’s Ferry, West Virginia

This is an aerial view of the historic Harper's Ferry, West Virginia.

Harper’s Ferry, West Virginia, is a historic town of only 250 people that looks like it came out of a storybook. The town is part of the Harper’s Ferry National Park and sits on the junction of the Potomac and Shenandoah rivers.

The famed Appalachian Trail also runs through the park, in addition to 20 miles of other scenic trails.  With museums, historic restaurants and shops, and plenty of scenery, this is a town people visit for history and nature.

La Crosse, Wisconsin

This is an aerial view of downtown La Crosse, Wisconsin.

La Crosse, Wisconsin, moves to a different drum than the rest of its state. With the Mississippi River snaking by, the place has an extra special aquatic touch. But there is still the skiing, the hiking, and all the other sportspeople visiting Wisconsin come to expect. But its biggest sporting draw is mountain biking.

La Crosse’s mountain biking community is so large that they have a Bicycle Festival. But even if you can’t make that, there is a monthly Beer By Bike Brigade you can join on a visit. Don’t worry if it is winter; they just switch to snow biking (fatbikers) on one of the many groomed winter trails.

La Crossee has a thriving arts and culture community. There is live music, theater, quilting, a variety of dancing, painters, and more. The place is known for its array of quality pubs, taverns, and fine restaurants. But don’t forget the sweets, and make a stop at their decadent Pearl Street Ice Cream.

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Manitou Springs, Colorado

This is a look at the houses and structures of Manitou Springs, Colorado.

Manitous Spring, Colorado, is a resort town of a little over 5,000 people. The eccentric town is nicknamed “Hippie Mayberry” and is nestled below Pikes Peak, full of Western-styled spirit. The area boasts eight different mineral springs. Like in Ashland, the public is granted free access to the water and welcome to taste each of their unique flavors.

The area is full of events that brim with characters, such as the annual Emma Crawford Coffin Races, January’s Fruitcake Toss, Mumbo Jumbo Gumbo Cook-Off, the Wine Festival, and numerous sporting events, such as the Pikes Peaks Marathon.  In addition, the area is full of artists, and there are plenty of galleries, studios, and co-ops where you can view their work.

Outdoor enthusiasts will be overwhelmed with options when it comes to ways to enjoy the Rocky Mountains. There are plenty of trails that will lead you up high, including the popular and breath-snatching Manitou Incline, where you rise 2,000 feet in elevation in under a mile. (Yeah, you might need to be a wee bit in shape for this one.) 

Missoula, Montana

This is an aerial view of the town of Missoula, Montana.

Missoula, Montana is a college town of 75,000 residents, surrounded by snow-capped peaks. Like Ashland, this is a place that brings you the great outdoors along with quirky local shots, fine dining, local breweries, with plenty of live music, art galleries, and theater. It’s an area where you have to try really hard to become bored.

The town always seems to have a festival occurring, including the Big Sky Documentary Film Festival, numerous sporting events, Kyi-Yo Pow Wow, Missoula Symphony In the Park, GermanFest, The Montana Book Festival, and so much more. 

Situated in the Northern Rockies, there are sporting events throughout the year to suit the seasons. In the summer, the area offers an abundance of water sports, hiking, and mountain biking. Winter brings ice skating, skiing, ice fishing, and even taking sleigh rides.

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Nantucket, Massachusetts

This is an aerial of Nantucket, Massachusetts with a view of the sea and harbor.

Nantucket, Massachusetts, is dressed in traditional New England, but the town of 11,000 is full of culture and arts. The town has numerous bookstores, museums, antique shops, galleries, and even visit the Lighthouse.

Like Ashland, the area hosts many festivals, including the Nantucket Wine & Food, the Daffodil FestivalNantucket Book Festival, Nantucket Film Festival, Nantucket Garden Festival, and the famed Race Week. Nor will you lack food, from casual eats, bakeries, markets, and fine dining; there is something for every palate, even if you don’t eat fish.

Outdoor lovers will appreciate the town’s numerous beaches and parks. Nor do you have to be a die-hard mountain biker to enjoy cycling around the island, and there are many places that rent wheels for the day. While the area is known for sailing and fishing, Nantucket even has its own surfing school. Visitors can sign up for lessons, too.

Newburyport, Massachusetts

This is an aerial view of the harbor area of Newburyport, Massachusetts.

Newburyport, Massachusetts, is a picturesque seaport 30 miles north of Boston. The town has nearly 18,000 residents and is full of seaside charm and good food full of character, such as Mad Martha’s Island Cafe. It also boasts plenty of shops and curiosities, including the Jabberwocky Bookshop.

The area has museums to visit, such as the Custom House Maritime Museum. If that makes you thirsty, you can sample one of the many local beers produced by their local breweries, such as Riverwalk Brewing. Or stop by one of their many coffee establishments, including Plum Island Coffee Roasters

Newport, Rhode Island

This is an aerial view of Newport, Rhode Island with a view of the beach.

Newport, Rhode Island, is a colorful seaside town of 25,000 that balloons during tourist season. Folks come to take a peek at bygone wealth, explore the cliff walks, enjoy the local wines, sail in their yacht, or take part in a sunset cruise.

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Newport is host to many music festivals from jazz to classic, and there are boat parades, boat shows, Newport Flower Show,  and the Newport Oyster & Chowder Festival. They also host many galleries, theaters, film festivals, and other cultural delights.

Olympia, Washington

This is an aerial view of the city of Olympia, Washington.

Olympia, Washington, is the quiet capital of the state. But the city of 51,000 people has much to love. The historic town is wealthy in architecture, including the Governor’s Mansion that gained its first brick in 1908, the Bigelow House Museum where Susan B. Anthony once famously dined,  and the 1904 Schmidt House.

Olympia is home to Olympia Artesian Vodka, Top Rung Brewing Co., Three Magnets Brewing Co., and Headless Mumby Brewing. You can also find great coffee at places such as Burial Grounds Coffee and the Dancing Goats. Also, if you enjoy trying local wines, there is plenty to try, including those from Medicine Creek Winery.

Like Ashland, Olympia is a community for nature lovers, and the Puget Sound is right there whenever you want to take a paddle around or spend time at the beach. There is also the Billy Frank Jr. Nisqually National Wildlife Refuge, Marathon Park, and the Yashiro Japanese Garden to explore.  

Park City, Utah

This is an aerial view of Park City, Utah with trees and mountains.

Park City, Utah, was launched to international fame thanks to the Sundance Film Festival. But there is more than that to this town of 8,375 people, especially if you are an outdoor enthusiast.

Winter delights include skiing, ice skating, dog sledding, snowboarding, sleigh rides, snow biking, and more. Warmer months are perfect for hot air ballooning, mountain biking, hiking, golf, and a slew of water sports.

Nor are the town’s cultural offerings limited to film. The Egyptian Theatre Company hosts a diverse lineup of live events, and the Beethoven Festival of Park City is the longest-running classical music festival in the state. 

Visitors can treat themselves to a historic wine tour with the Fox School of Wine or explore the High West Distillery. They can also check out the state’s first artist-founded gallery at Artworks Park City and brows Dolly’s Bookstore.

To eat, there are a plethora of delicious options such as family-owned Hearth and Hill or, if you are craving American cuisine, dig in at Handle. If you want to soak up luxurious food and views, there is the Glitretind & Troll Hallen Lounge at Stein Eriksen Lodge. Or stay on the main street and enjoy local favorite Grappa.

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Port Townsend, Washington

This is an aerial view of Ferry Water street in Port Townsend, Washington.

Port Townsend, Washington, is a coastal town of 9,500 people decked out in Victorian architecture. It’s a book lovers paradise, with numerous cafes and bookstores, including Phoenix Rising, rare book collector William James Bookseller, and Imprint Bookstore that is home to The Writers’ Workshoppe.

Port Townsend is a walkable town that doesn’t require a car to enjoy. It offers plenty of fun places, including the Bazaar Girls, Sirens Pub, and the Wooden Boat Festival.  You can enjoy boat tours and kayak rentals from the Northwest Maritime Center. There you can choose a relaxing day or, if you sign up in time, take part in the Race to Alaska, known as the A2KA.   

For those wanting to go further afield but avoid Alaska, Port Townsend is right by the Fort Worden State Historical Park, where the mountainous forest meets the Puget Sound. A little hour away, there is the world-renowned Olympic National State Park. The park covers almost a million acres, stretching from glacier-capped mountains to over 70 miles of coastline.

Savannah, Georgia

This is an aerial view of the downtown area of Savannah, Georgia.

Savannah, Georgia, is a city of 150,000 residents that is full of old-timey Southern elegance and sprawling fragrant gardens. Considered the cultural hub of the state, there is much to explore, including the Jepson Center,  live music, haunted buildings, and the famous City Market.

This is a city for folks who love Ashland but want some elbow room. Festivals are always happening, including the annual Savannah Jazz Festival, Oktoberfest, Savannah Music Festival, Savannah Film Festival, marathons,  and so much more.

Eating well is practically a religion in this city. The Congress Street Social Club dishes up live music, good food and even has a paw-friendly patio. There is pizza at Vinnie Van Go-Go’s, take a seat at the historic Pirates’ House, enjoy the acclaimed shrimp and grits at Vic’s On The River, and visit Leopold’s Ice Cream that’s been dishing up since 1919.

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St. Francisville, Louisiana

This is a street view of the corner house in St. Francisville, Louisiana.

St. Francisville, Louisiana, is a charming hideaway of only 2,000 residents. Their historic district is as saturated in history as the area’s gardens are in lush greenery. Ghost hunters will be drawn to the Myrtles Plantation, while horticultural enthusiasts will want to take in the Afton Villa Gardens.  

Those craving rugged nature can immerse themselves in the Tunica Hills Wildlife Management Area. Outside of hunting season, the area is popular with birdwatchers, photographers, bicyclists, and horseback riders. Local events include Feliciana Hummingbird Celebration, Jeep Jamboree, and the Angola Prison Rodeo.

Sun Valley, Idaho

This is an aerial view of Sun Valley, Idaho during winter with a view of the mountains.

Sun Valley, Idaho, is a resort town of 2,000 people that visitors flock to for the outdoors, wellness, and cultural delights. The isolated town is located up near Bald Mountain and Dollar Mountain, where people can ski in the winter.

Come summer, the area is known for hiking, horseback riding, and mountain biking. People also enjoy water sports, including rafting, tubing, and kayaking. But for those wanting a slower pace, there is fishing and hot springs, too.

The area doesn’t have Ashland’s Shakespeare Festival. But it is known for its Writer’s Conference, the Sun Valley Film Festival, its live theater companies, numerous art galleries, and its free summer symphony concerts. However, the best show is at night when the lights go out, and the area unleashes its astounding night sky littered with stars.