Smalltown America: The Prettiest Small Towns Everyone Should Visit

There’s always a tiny town you’ve perhaps 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. Some of these small towns are full of charm, and people can’t help but visit them over and over again.

1. Hana, Hawaii

Image Credit: Shutterstock.

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.

2. Angwin, California

Angwin, California
Image Credit: CC BY-SA 3.0/Wiki Commons.

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.

3. Sedona, Arizona

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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 that surrounds the town.

4. Madison, Indiana

Main Street, Madison, Indiana
Image Credit: Warren LeMay – CC0/Wiki Commons.

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
Image Credit: Derek Ramsey, Own Work – GFDL 1.2/Wiki Commons.

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

Image Credit: Wiki Commons.

Many people rave about how pretty New Hope is. Boutique shops line the river, and the restaurants, craft stores, and museums make the New Hope popular over weekends.

7. West Yellowstone, Montana

Yellowstone Avenue in West Yellowstone, Montana
Image Credit: CC BY-SA 3.0/Wiki Commons.

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 the Yellowstone National Park frames the town, which sees over 4 million visitors yearly.

8. Mendocino, California

Mendocino, California
Image Credit: Jef Poskanzer – CC BY 2.0/Wiki Commons.

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

Yampa in Steamboat Springs
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Imagine a town sprinkled with champagne powder smooth snow that looks like frosting on a gingerbread house. The majestic mountains are perfect for skiing, which is why so many people flock here each winter.

10. Hood River, Oregon

Hood River, Oregon
Image Credit: Sam Beebe – CC BY 2.0/Wiki Commons.

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 Columbia River Gorge, making this small town an easy choice as one of the prettiest towns in America.

11. Galena, Illinois

Main Street, Galena, Illinois, United States.
Image Credit: Julien Scavini, Own Work – CC BY-SA 4.0/Wiki Commons.

Galena is described as surprisingly delightful with its quaint boutiques and restaurants. Another traveler even said the small town felt like a postcard. It’s known to have a number of well-preserved 19th-century buildings that people can explore and take history lessons.

12. Port Townsend, Washington

Bartlett House Port Townsend, Washington
Image Credit: Adbar, Own Work – CC BY-SA 3.0/Wiki Commons.

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.

13. Exeter, New Hampshire

Exeter High School
Image Credit: Austin Blake Grant, Own Work – CC BY-SA 3.0/Wiki Commons.

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

Sleepy Hollow Cemetery Concord, Massachusetts
Image Credit: Kenneth C. Zirkel, Own Work – CC BY-SA 4.0/Wiki Commons.

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

15. Manitou Springs, Colorado

Manitou Springs
Image Credit: Carole Henson, Own Work – CC BY-SA 3.0/Wiki Commons.

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

Abiquiu, New Mexico
Image Credit: CC BY 2.0/Wiki Commons.

Abiquiu is a stunning region within Rio Arriba County, home to 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

Cape Neddick Light, York, Maine
Image Credit: Michael Murphy – CC BY 2.0/Wiki Commons.

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

18. Jackson, New Hampshire

Jackson, New Hampshire, USA
Image Credit: Wiki Commons.

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

Connecticut River Museum, Essex, Connecticut
Image Credit: Joe Mabel – CC BY-SA 3.0/Wiki Commons.

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

United States Post Office, Deerfield, Massachusetts
Image Credit: Wiki Commons.

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 town, and visitors can pop into the museums that showcase Deerfield’s history.

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