The Experts' Picks for Prettiest Towns in America

Travel writers, photographers, and an urban designer selected by Forbes have named the 20 prettiest towns in America; their varied definitions of "prettiness" are reflected in their choices.

1 minute read

October 22, 2008, 12:00 PM PDT

By Judy Chang


"Identifying America's prettiest towns is by definition a subjective undertaking-prettiness, to adapt an old saying, is in the eye of the beholder. So when we asked five experts for their lists of the country's prettiest towns, we left the definition of 'pretty' up to the judges themselves."

"Danno Glanz, an urban designer with the Berkeley, Calif.-based urban design, community planning and architecture firm Calthorpe Associates, says he gravitates toward 'places that have an exceptional, unique urban form.' Glanz says that in lieu of a traditionally pretty town like Carmel, Calif., 'which has a lot of flower boxes on windows,' he'd opt instead to visit someplace like the southern Arizona enclave of Bisbee, whose cottages and bungalows form 'eclectic hillside residential neighborhoods that terrace down the hillside in an organic way.'"

"While the 20 towns here comprise a diverse array of locations, sizes and architectural styles, our expert's selections lean heavily toward the East, and New England picks figure prominently in their selections. Three of our five panelists chose New Hampshire towns (Portsmouth and Hanover) as among the nation's prettiest, and destinations in Maine, Vermont and Rhode Island are also sprinkled among the experts' choices."

Tuesday, October 7, 2008 in Forbes Traveler

portrait of professional woman

I love the variety of courses, many practical, and all richly illustrated. They have inspired many ideas that I've applied in practice, and in my own teaching. Mary G., Urban Planner

I love the variety of courses, many practical, and all richly illustrated. They have inspired many ideas that I've applied in practice, and in my own teaching.

Mary G., Urban Planner

Cover CM Credits, Earn Certificates, Push Your Career Forward

Aerial view of town of Wailuku in Maui, Hawaii with mountains in background against cloudy sunset sky.

Maui's Vacation Rental Debate Turns Ugly

Verbal attacks, misinformation campaigns and fistfights plague a high-stakes debate to convert thousands of vacation rentals into long-term housing.

July 1, 2025 - Honolulu Civil Beat

Logo for Planetizen Federal Action Tracker with black and white image of U.S. Capitol with water ripple overlay.

Planetizen Federal Action Tracker

A weekly monitor of how Trump’s orders and actions are impacting planners and planning in America.

July 2, 2025 - Diana Ionescu

White and purple sign for Slow Street in San Francisco, California with people crossing crosswalk.

San Francisco Suspends Traffic Calming Amidst Record Deaths

Citing “a challenging fiscal landscape,” the city will cease the program on the heels of 42 traffic deaths, including 24 pedestrians.

July 1, 2025 - KQED

Google street view of wide street in Cleveland, Ohio with blue 55th Street sign and red brick three-story building visible in right corner.

Cleveland to Boost Bike Safety With New Bike Lanes, School Programs

The program, using curriculum created by Cleveland Bikes, is part of a broader effort to improve safety along school routes.

5 seconds ago - Signal Cleveland

Aerial view of heavily damaged mobile homes after a hurricane in Florida.

Florida Home Insurers Disproportionately Dropping Low-Income Households

Non-renewal rates are highest in inland counties, not the coastal areas most immediately vulnerable to storms.

1 hour ago - Inside Climate News

"Altadena - Not For Sale" yard sign in front of burned down house after Eaton Fire in Altadena, California in January 2025.

Half of Post-Fire Altadena Home Sales Were to Corporations

Large investors are quietly buying up dozens of properties in Altadena, California, where a devastating wildfire destroyed more than 6,000 homes in January.

July 7 - Dwell

Urban Design for Planners 1: Software Tools

This six-course series explores essential urban design concepts using open source software and equips planners with the tools they need to participate fully in the urban design process.

Planning for Universal Design

Learn the tools for implementing Universal Design in planning regulations.

Associate/Senior Planner

Gallatin County Department of Planning & Community Development

Senior Planner

Heyer Gruel & Associates PA