From gorgeous coastal villages to close-knit farming communities, there are charming small towns in Oregon full of amazing history, beautiful scenery, vibrant downtowns, and great people. Today we’re shining the spotlight on some of the absolute coolest small towns in Oregon, some of which are total under-the-radar hidden gems!
- Silverton
flickr/ Edmund Garman Silverton is the epitome of a beautiful small town. Located in Marion County near the amazing Silver Falls State Park, this wonderful place is full of small town charm AND it’s surrounded by stunning scenery. Silverton, OR 97381, USA
- Coos Bay
flickr/ Pat Kight Coos Bay is a charming coastal town in northern Coos County. This beautiful place has great restaurants, beautiful scenery and more. It really is one in a million. Coos Bay, OR, USA
- Brownsville
flickr/ Jasperdo Brownsville is a beautiful historic town in Linn County that is truly delightful, and totally famous – it’s the location for the ’80s hit Stand By Me! Brownsville, OR 97327, USA
- Drain
flickr/ Sandy Horvath-Dori What better sums up Drain’s small-town charm than this photo of it’s very own covered bridge? This wonderful small town town in Douglas County is absolutely enchanting. Drain, OR, USA
- Florence
flickr/ Stephanie Sarles This small, coastal town in Lane County is truly remarkable. With incredible restaurants, a bustling, historical downtown, beautiful beaches, and more, Florence is a gorgeous town that everyone will enjoy. Florence, OR 97439, USA
- Talent
flickr/ Miguel Tejada-Flores This small town in Jackson County is home to an annual harvest festival, wonderful small businesses, friendly locals, and plenty of sunshine. Oh, and an amazing hidden gem restaurant, too! Talent, OR 97540, USA
- Coquille
flickr/ Jan Tik This picturesque town in Coos County will blow you away with its warm climate, lovely architecture, local theater, and more. Coquille, OR 97423, USA
- Aurora
flickr/ Jasperdo Located in Marion County, this wonderful town has less than 1,000 residents, but it certainly doesn’t lack in charm. When you’re visiting, be sure to check out the Old Aurora Museum and the Mainstreet Merchantile Antique store. Aurora, OR 97002, USA
- Carlton
flickr/ neighorn Located in the heart of wine country is the delightful town of Carlton. This historical farming town has lots to offer, and it’s a perfect place to have an authentic experience of the splendor of the Willamette Valley. Carlton, OR 97111, USA
- Baker City
flickr/ Ken Lund The lovely Baker City is located in eastern Oregon. Its historical buildings, beautiful scenery and vibrant culture make it a wonderful place to visit. Baker City, OR 97814, USA
- Bandon
flickr/ m01229 Oh, Bandon. What a beautiful, charming place. In 2010, BugdetTravel named this coastal town in Coos County one of the “Coolest Small Towns in America”, and for good reason. Bandon, OR 97411, USA
- Vernonia
flickr/ B J IMAGERY Vernonia is an incredible, lively little city located on the Nehalem River in Columbia County. The town’s logging roots are still visible today, which you can admire while day tripping through this quaint little town. Vernonia, OR 97064, USA
- Wheeler
flickr/ Doug Kerr Wheeler is an enchanting village located where the coast meets the gorgeous Nehalem River in Tillamook County. While you’re in the area, be sure to stop by the iconic Tillamook Creamery for a next-level shake or sundae! Wheeler, OR, USA
- Paisley
flickr/ Michael (a.k.a. moik) McCullough This lovely little town is located in Lake County and has a teensy tiny population of 243 residents. It’s also one of the friendliest small towns in the state! Paisley, OR 97636, USA
- Riddle
flickr/ Kirsten Comandich Located in Douglas County, Riddle is a lovely place with a nostalgic, small town feel – and some amazing restaurants and bakeries! Riddle, OR 97469, USA
- Brookings
flickr/ Tomas Bozack Brookings is a wonderful coastal town in Curry County with incredible restaurants, a friendly community, and an incredible coastline dotted with sea stacks. Brookings, OR 97415, USA
- Astoria
flickr/ David Grant Astoria is one of the larger towns on this list, but we decided it deserved to be included because it’s just so darn delightful. Here you’ll find beautiful scenery, gorgeous architecture, fascinating history, and more. Also, it’s the oldest town in Oregon, which automatically earns it major coolness credibility! Astoria, OR 97103, USA
- Joseph
flickr/ Bruce Fingerhood Nestled in the stunning Wallowa Mountains is the incredible, vibrant town of Joseph. This is a great place to stay whether you want to explore the great outdoors or soak in the comforts of small town living—or both. Joseph, OR 97846, USA
- Gold Beach
flickr/ Ken Lund Gold Beach is a delightful little coastal locale located in Curry County. With a population of just over 2,000, this unique seaside village is full of small town charm and extraordinary natural beauty. Gold Beach, OR 97444, USA
- Sisters
flickr/ Jonathan Named after the three volcanos that loom gorgeously nearby, Sisters is a wonderful small town surrounded by natural beauty. Sisters also has a vibrant downtown full with great cafes, shops, restaurants and more. Sisters, OR 97759, USA
- Oakland
flickr/ Megan Located in the lovely Douglas County, Oakland is an enchanting little place with a distinct small-town charm. Oakland, OR 97462, USA
What’s on your list of the coolest small towns in Oregon? Did we miss any of your favorite little locales? Share them in the comments below, or nominate your favorite town for a chance to be featured in an upcoming article!
flickr/ Edmund Garman
Silverton is the epitome of a beautiful small town. Located in Marion County near the amazing Silver Falls State Park, this wonderful place is full of small town charm AND it’s surrounded by stunning scenery.
Silverton, OR 97381, USA
flickr/ Pat Kight
Coos Bay is a charming coastal town in northern Coos County. This beautiful place has great restaurants, beautiful scenery and more. It really is one in a million.
Coos Bay, OR, USA
flickr/ Jasperdo
Brownsville is a beautiful historic town in Linn County that is truly delightful, and totally famous – it’s the location for the ’80s hit Stand By Me!
Brownsville, OR 97327, USA
flickr/ Sandy Horvath-Dori
What better sums up Drain’s small-town charm than this photo of it’s very own covered bridge? This wonderful small town town in Douglas County is absolutely enchanting.
Drain, OR, USA
flickr/ Stephanie Sarles
This small, coastal town in Lane County is truly remarkable. With incredible restaurants, a bustling, historical downtown, beautiful beaches, and more, Florence is a gorgeous town that everyone will enjoy.
Florence, OR 97439, USA
flickr/ Miguel Tejada-Flores
This small town in Jackson County is home to an annual harvest festival, wonderful small businesses, friendly locals, and plenty of sunshine. Oh, and an amazing hidden gem restaurant, too!
Talent, OR 97540, USA
flickr/ Jan Tik
This picturesque town in Coos County will blow you away with its warm climate, lovely architecture, local theater, and more.
Coquille, OR 97423, USA
Located in Marion County, this wonderful town has less than 1,000 residents, but it certainly doesn’t lack in charm. When you’re visiting, be sure to check out the Old Aurora Museum and the Mainstreet Merchantile Antique store.
Aurora, OR 97002, USA
flickr/ neighorn
Located in the heart of wine country is the delightful town of Carlton. This historical farming town has lots to offer, and it’s a perfect place to have an authentic experience of the splendor of the Willamette Valley.
Carlton, OR 97111, USA
flickr/ Ken Lund
The lovely Baker City is located in eastern Oregon. Its historical buildings, beautiful scenery and vibrant culture make it a wonderful place to visit.
Baker City, OR 97814, USA
flickr/ m01229
Oh, Bandon. What a beautiful, charming place. In 2010, BugdetTravel named this coastal town in Coos County one of the “Coolest Small Towns in America”, and for good reason.
Bandon, OR 97411, USA
flickr/ B J IMAGERY
Vernonia is an incredible, lively little city located on the Nehalem River in Columbia County. The town’s logging roots are still visible today, which you can admire while day tripping through this quaint little town.
Vernonia, OR 97064, USA
flickr/ Doug Kerr
Wheeler is an enchanting village located where the coast meets the gorgeous Nehalem River in Tillamook County. While you’re in the area, be sure to stop by the iconic Tillamook Creamery for a next-level shake or sundae!
Wheeler, OR, USA
flickr/ Michael (a.k.a. moik) McCullough
This lovely little town is located in Lake County and has a teensy tiny population of 243 residents. It’s also one of the friendliest small towns in the state!
Paisley, OR 97636, USA
flickr/ Kirsten Comandich
Located in Douglas County, Riddle is a lovely place with a nostalgic, small town feel – and some amazing restaurants and bakeries!
Riddle, OR 97469, USA
flickr/ Tomas Bozack
Brookings is a wonderful coastal town in Curry County with incredible restaurants, a friendly community, and an incredible coastline dotted with sea stacks.
Brookings, OR 97415, USA
flickr/ David Grant
Astoria is one of the larger towns on this list, but we decided it deserved to be included because it’s just so darn delightful. Here you’ll find beautiful scenery, gorgeous architecture, fascinating history, and more. Also, it’s the oldest town in Oregon, which automatically earns it major coolness credibility!
Astoria, OR 97103, USA
flickr/ Bruce Fingerhood
Nestled in the stunning Wallowa Mountains is the incredible, vibrant town of Joseph. This is a great place to stay whether you want to explore the great outdoors or soak in the comforts of small town living—or both.
Joseph, OR 97846, USA
Gold Beach is a delightful little coastal locale located in Curry County. With a population of just over 2,000, this unique seaside village is full of small town charm and extraordinary natural beauty.
Gold Beach, OR 97444, USA
flickr/ Jonathan
Named after the three volcanos that loom gorgeously nearby, Sisters is a wonderful small town surrounded by natural beauty. Sisters also has a vibrant downtown full with great cafes, shops, restaurants and more.
Sisters, OR 97759, USA
flickr/ Megan
Located in the lovely Douglas County, Oakland is an enchanting little place with a distinct small-town charm.
Oakland, OR 97462, USA
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The OIYS Visitor Center
Coolest Small Towns in Oregon August 30, 2021 Sarah What’s the coolest small town in Oregon? Well, ‘cool’ is relative, but we think everyone can agree that Jacksonville is the coolest small town in Oregon! Nestled in the heart of Southern Oregon’s Wine Country, Jacksonville is a small town that’s big on charm – and coolness. For starters, Jacksonville is home to an epic music festival, which is peak cool vibes. It’s also full of history; its downtown Historic District is actually listed on the National Registrar of Historic Places, in fact! And Jacksonville is also peak Beaver State beauty, as its location in Wine Country means lots of lovely scenery and wonderful opportunities for outdoor recreation… and wine tasting! What’s the quirkiest town in Oregon? In a state that’s known for keeping it weird, there are numerous small towns in Oregon full of quirky charm. We’re big fans of Ashland, a place that’s well-known for its thriving arts scene and free-spirited community. The centerpiece of the town is the Oregon Shakespeare Festival. Founded in 1935, this live theatre venue is straight out of the 1600s, complete with the troupe’s iconic outdoor Allen Elizabethan Theatre, which opens in early June and runs through mid-October. We recommend checking the company’s schedule and planning a little weekend getaway full of theatre and small-town charm! What are some of the best small towns in Oregon to visit? Oregon’s larger cities may get most of the spotlight, but The Beaver State’s small towns are nothing short of wonderful. All across the state, there are some downright delightful small towns that really exemplify peak Oregon living. Whether it’s a charming coastal city, small mountain municipality, wine country province, or a little locale in the state’s rugged outback, Oregon has some of the most winsome small towns in the PNW. Here are eight small towns in Oregon that are just perfect for a weekend escape – we challenge you to visit (and be charmed by) them all!
The OIYS Visitor Center
Coolest Small Towns in Oregon
August 30, 2021
Sarah
What’s the coolest small town in Oregon? Well, ‘cool’ is relative, but we think everyone can agree that Jacksonville is the coolest small town in Oregon! Nestled in the heart of Southern Oregon’s Wine Country, Jacksonville is a small town that’s big on charm – and coolness. For starters, Jacksonville is home to an epic music festival, which is peak cool vibes. It’s also full of history; its downtown Historic District is actually listed on the National Registrar of Historic Places, in fact! And Jacksonville is also peak Beaver State beauty, as its location in Wine Country means lots of lovely scenery and wonderful opportunities for outdoor recreation… and wine tasting! What’s the quirkiest town in Oregon? In a state that’s known for keeping it weird, there are numerous small towns in Oregon full of quirky charm. We’re big fans of Ashland, a place that’s well-known for its thriving arts scene and free-spirited community. The centerpiece of the town is the Oregon Shakespeare Festival. Founded in 1935, this live theatre venue is straight out of the 1600s, complete with the troupe’s iconic outdoor Allen Elizabethan Theatre, which opens in early June and runs through mid-October. We recommend checking the company’s schedule and planning a little weekend getaway full of theatre and small-town charm! What are some of the best small towns in Oregon to visit? Oregon’s larger cities may get most of the spotlight, but The Beaver State’s small towns are nothing short of wonderful. All across the state, there are some downright delightful small towns that really exemplify peak Oregon living. Whether it’s a charming coastal city, small mountain municipality, wine country province, or a little locale in the state’s rugged outback, Oregon has some of the most winsome small towns in the PNW. Here are eight small towns in Oregon that are just perfect for a weekend escape – we challenge you to visit (and be charmed by) them all!
The OIYS Visitor Center
The OIYS Visitor Center
Well, ‘cool’ is relative, but we think everyone can agree that Jacksonville is the coolest small town in Oregon! Nestled in the heart of Southern Oregon’s Wine Country, Jacksonville is a small town that’s big on charm – and coolness. For starters, Jacksonville is home to an epic music festival, which is peak cool vibes. It’s also full of history; its downtown Historic District is actually listed on the National Registrar of Historic Places, in fact! And Jacksonville is also peak Beaver State beauty, as its location in Wine Country means lots of lovely scenery and wonderful opportunities for outdoor recreation… and wine tasting!
What’s the quirkiest town in Oregon?
In a state that’s known for keeping it weird, there are numerous small towns in Oregon full of quirky charm. We’re big fans of Ashland, a place that’s well-known for its thriving arts scene and free-spirited community. The centerpiece of the town is the Oregon Shakespeare Festival. Founded in 1935, this live theatre venue is straight out of the 1600s, complete with the troupe’s iconic outdoor Allen Elizabethan Theatre, which opens in early June and runs through mid-October. We recommend checking the company’s schedule and planning a little weekend getaway full of theatre and small-town charm!
What are some of the best small towns in Oregon to visit?
Oregon’s larger cities may get most of the spotlight, but The Beaver State’s small towns are nothing short of wonderful. All across the state, there are some downright delightful small towns that really exemplify peak Oregon living. Whether it’s a charming coastal city, small mountain municipality, wine country province, or a little locale in the state’s rugged outback, Oregon has some of the most winsome small towns in the PNW. Here are eight small towns in Oregon that are just perfect for a weekend escape – we challenge you to visit (and be charmed by) them all!
