20 Prettiest Small Towns in America for Your Bucket List

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There’s always a tiny town you’ve driven through, visited over a weekend getaway, or maybe even used to live in that immediately comes to mind when someone talks about a pretty small town they stumbled upon.

A group of people were asked about the prettiest small towns in America, and these are the 20 answers they gave.

1. Galena, Illinois

galena illinois

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Galena was described as surprisingly delightful with its quaint boutiques and restaurants. Another traveler even said the small town felt like a postcard. 

2. Port Townsend, Washington

port townsend washington

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Port Townsend in Washington is one traveler’s favorite small town as it has Victorian architecture, which always gives a place a royal feel. Port Townsend sits along Puget Sound, known for its natural beauty and wildlife. 

3. Sedona, Arizona

holy cross sedona

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Sedona ranks at the top of the list as one of the nation’s best destinations. The natural landscape surrounding it makes it so pretty, including the desert juniper forest and the iconic red rock. 

4. Madison, Indiana

madison indiana

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Walk through history when you visit Madison, Indiana. Its nineteenth and twentieth-century architectural styles will make you feel like you’re in an old movie. Madison’s crowned jewel is Clifty Fall State Park, where you can splash around in the many refreshing waterfalls.

5. Jim Thorpe, Pennsylvania

jim thorpe pennsylvania

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Surrounded by incredible landscapes, Jim Thorpe is a top tourist spot for outdoor adventures like hiking, whitewater rafting, and mountain biking. The town has lovely historical monuments, museums, Victorian-era architecture, and landscapes. 

6. New Hope, Pennsylvania

new hope pennsylvania

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Many people rave about how pretty New Hope is. A water source always adds a peaceful element to a place, which is what the river does for this small town. Boutique shops line the river, and the restaurants, craft stores, and museums make the New Hope popular over weekends. 

7. West Yellowstone, Montana

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West Yellowstone is a gateway community to the national park, so of course, it’s considered one of the prettiest towns in America. The glorious scenery of Yellowstone National Park frames the town, which sees over four million visitors yearly. 

8. Mendocino, California

Magical Redwoods National Park, California

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A nature-infused town will always be pretty. Mendocino is no exception, boasting the world’s smallest and largest Redwood trees, idyllic oceanfront botanical gardens, and glass beaches.

9. Steamboat Springs, Colorado

Best breweries in Colorado

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Imagine a town sprinkled with champagne powder smooth and light snow that looks like frosting on a gingerbread house. Majestic mountains, perfect for skiing, frame Steamboat Springs and make the town look like a children’s storybook.

10. Hood River, Oregon

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Mount Hood watches over the town of Hood River and looks even more beautiful when dusted in snow. Hood River is located on the banks of the Columbia River Gorge, making this small town an easy choice as one of the prettiest towns in America. 

11. Hana, Hawaii

Snorkeling paradise Hanauma Bay, Oahu, Hawaii

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Hana in Hawaii is a natural haven with lush vegetation and rolling hills. It boasts the Hana Beach Park, Pailoa Bay, Hamoa Beach, and the Kaia Ranch Tropical Botanical Gardens.

12. Angwin, California

castello amorosa angwin california

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If wine makes a town pretty, then Angwin is ravishing. This gorgeous town sits close to the summit of Mount Howell, a worthwhile uphill drive for wine tastings at the many vineyards in the area. 

13. Exeter, New Hampshire

exeter new hampshire

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Exeter is a picturesque town brimming with history and beautiful old buildings. Nature is also prevalent in this pretty town, with Swasey Parkway stealing the attention of all those who visit. 

14. Concord, Massachusetts

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Locals and visitors love Concord for its vast open spaces that invite exploration. The town turns deep shades of reds, oranges, and yellows as fall sets in and makes the perfect backdrop to the quaint old-style buildings that line the streets.

15. Manitou Springs, Colorado

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Refreshing natural mineral springs are scattered throughout the historic town of Manitou Springs. Experience the natural magic of a town cozily nestled between Pikes Peak and the Garden of the Gods. 

16. Abiquiu, New Mexico

night sky stars new mexico

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Abiquiu is a stunning region within the Rio Arriba County with its Echo Amphitheatre and Abiquiu Lake. Many people believe it’s the prettiest town in New Mexico, and you’ll agree when you see it.

17. York, Maine

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A seaside town has that lazy, laid-back feel and endless ocean views hitting the horizon. York is one of those places with stately cliffside homes that look over the sea and turn a magical golden color as the sun sets. 

18. Jackson, New Hampshire

new hampshire autumn white mountains

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Jackson is one of those pretty small towns with many things to do and views that leave you breathless. It’s a White Mountain gem with farmland scenes and old steeple churches that people love returning to. 

19. Essex, Connecticut

essex connecticut

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Walk down the quaint streets of Essex and take in the fascinating architecture, the blooming gardens, giant trees, and gorgeous landscapes that unfold from the town. Visitors can’t get over this picturesque town situated along the Connecticut River.

20. Deerfield, Massachusetts

deerfield massachusetts

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Deerfield is a leaf peeper’s paradise, as its majestic trees color the town red, orange, and yellow in the fall. The Deerfield River runs through the city, and visitors can pop into the museums that showcase Deerfield’s history.

Where indicated, some images courtesy of Depositphotos.com.

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Jordy Johnson

Jordy gave up her home base to travel South Africa and experience more of her country. From that decision, she’s landed work as a travel writer for a magazine that showcases southern Africa and has grown her Instagram travel page, WeTheWests. She enjoys showing locals and foreigners all the beautiful and unique places and experiences South Africa and the rest of the world have to offer.