| AWARD/ACCOLADE | PUBLICATION | DATE |
| | |
| Best Places To Live In American 2017 | Parade Magazine | 2017 |
| CNN | 2017 |
| 15 Reasons to Drop Everything and Move to This One Virginia City | Only in Your State | 2016 |
| The 25 Most Livable U.S. Cities in 2016 | Fiscal Times | 2016 |
| Why Charlottesville, Virginia Is A Hidden Travel Gem | Forbes | 2016 |
| 20 Most Beautiful College Campuses in America | Conde Nast Traveler | 2016 |
| Top 10 Places to Retire | Washington’s Top News | 2015 |
| Top 100 Best Places To Live | Livability | 2015 |
| #1 Most Beautiful College Campus in America | Best College Reviews | 2015 |
| 12 Cutest Small Towns in America | The Huffington Post | 2015 |
| The USA’s 12 Best Places for Book Lovers | The Culture Trip | 2015 |
| 7 Amazing Destination Bike Rides: Road Edition | bikewagon | 2015 |
| #7 Best College Town in America for Food and Drink | Thrillist | 2015 |
| 5 Wine Regions With a Unique Claim to Fame | Trivago & The Huffington Post | 2015 |
| 22 Best Small Town Family Weekend Destinations | Vacationidea.com | 2015 |
| The 9 Most Romantic Cities in the South | The Huffington Post | 2015 |
| Best Spring Marathons in the U.S. | Daily Burn | 2015 |
| #1 Most Beautifl College in the South | Best Colleges Online | 2015 |
| Best Places To Travel in 2015 | Orbitz | 2015 |
| 5 Best College Towns You’ll Be Interested in Moving To | Examiner | 2014 |
| America’s Best College Towns - #3 | Time Magazine | 2014 |
| America’s Best Towns for the Holidays | Travel + Leisure | 2014 |
| Brightest Fall Foliage Destinations in the Country | USA Today/10 Best | 2014 |
| #9 Best College Town Weekend | USA Today/10 Best | 2014 |
| 10 College Towns We’d Actually Want to Visit as Adults | Conde Nast Traveler | 2014 |
| Top 3 MBA Schools in the World | The Economist | 2014 |
| Virginia - Food Region of 2014 | Esquire | 2014 |
| #1 Fall Travel Destination | betterRVing.com | 2014 |
| Americas Most Iconic College Campuses - #1 | Brandpoint | 2014 |
| 10 Best College Towns 2014 | Livability | 2014 |
| The 50 Best College Towns in America | Best College Reviews | 2014 |
| Top 100 Best Places to Live | Livability | 2014 |
| Happiest City in America | Good Housekeeping | 2014 |
| America’s 5 New Foodie Cities | Wine Enthusiast | 2014 |
| #1 College Town in the Country | Travelers Today | 2014 |
| #1 Most Exciting Place in Virginia | Movoto | 2014 |
| 5 Destinations Every American Should Visit | Luxury Travel Magazine | 2014 |
| 10 Hidden Gems Among U.S. College Towns | Homeinsurance.com | 2014 |
| America’s Favorite Mountain Towns | Travel & Leisure | 2014 |
| 5 College Towns That Offer Way More Than Education | FlipKey | 2014 |
| 9 Southern Towns You’re Forgetting About But Shouldn’t | Huffington Post | 2014 |
| Happiest and Healthiest Cities in America | Business Insider | 2014 |
| 10 Best College Towns in America | Movoto | 2014 |
| America’s 10 Friendliest Small Cities | Movoto | 2014 |
| Top 10 Cities for Affordable Healthcare | Livability.com | 2014 |
| Six Exciting Wine Regions to Explore in 2014 | Forbes | 2014 |
| 15 Best Spring Marathons in the U.S. | Daily Burn | 2014 |
| America’s 10 Healthiest Small Cities | Daily Finance | 2014 |
| 6 Best Small Towns in America - Best Food Category | Huffington Post | 2014 |
| Top 9 Harvest Destinations in the World | Fodors | 2013 |
| Top 9 Small College Towns to Visit This Fall | Huffington Post | 2013 |
| Top 10 Wine Tasting Vacation Destinations in the World | Famouswonders.com | 2013 |
| Top 30 Places to Live in America | Livability.com | 2013 |
| One of the 15 Most Beautiful Campus’ in the World (UVA) | Forbes | 2013 |
| Top 10 Best Up and Coming Wine Region | NerdTravel | 2013 |
| Top 13 Best Historical Destinations in the United States | U.S. News | 2013 |
| Place Every American Should See | The Today Show | 2013 |
| Top 10 Spring Vacations in the World | Travel Channel | 2013 |
| #1 Medium Sized Mountain Town | Blue Ridge County Magazine | 2013 |
| Top 6 Great American Wine Region | Budget Travel | 2013 |
| Top 10 City in American for History Buffs | Travel Nerd | 2013 |
| #4 Most Romantic City in America | Livability.com | 2013 |
| Top 10 Wine Destination in the World | Wine Enthusiast | 2012 |
| American’s Prettiest Winter Towns | Travel & Leisure Magazine | 2012 |
| Top 10 Metro Areas Where People Indicate They Have the Best Overall Sense of Well-Being | USA Today | 2012 |
| Top "Brainiest" Metropolitan Areas | The Atlantic | 2012 |
| Best Small Places to Do Business - Rank 22 | Forbes Magazine | 2012 |
| Runner Up - Best For Food | USA Today/Rand McNally | 2012 |
| 25 Most Beautiful Schools (UVA) | Newsweek | 2012 |
| A Winemaking Frontier | Bloomberg News | 2012 |
| Smartest City in America | The Daily Beast | 2012 |
| #1 Agritourism Spot in America | Go Green Travel Green | 2012 |
| University of Virginia One of It’s 17 "World’s Most Beautiful Universities" | Travel & Leisure Magazine | 2012 |
| Top 20 Tailgate Town | Southern Living | 2012 |
| #10 Wine Vacation Spot in the World | US News | 2012 |
| The South’s Best College Towns | Southern Living | 2012 |
| The Best Southern Tailgates | Southern Living | 2012 |
| Tastiest Towns in the South - #5 | Southern Living | 2011 |
| #1 City to Live in the Country | Yahoo Real Estate/Sperling | 2011 |
| #4 for Book Lovers | Livability.com | 2011 |
| "Locavore" Capital of the World | Forbes Magazine | 2011 |
| Most Walkable City in Virginia | Walk Score | 2011 |
| Top 10 Charming Towns | Trip Advisor | 2011 |
| Healthiest Place to Live | Men’s Journal Magazine | 2010 |
| Top Place to Retire | Kiplinger Magazine | 2010 |
| 4th Best Place to Live in the Country | Kiplinger Magazine | 2009 |
| 11th Best Place to Find a Job | Forbes Magazine | 2009 |
| One of the 30 Coolest Neighborhoods (Belmont) | Men’s Health Magazine | 2009 |
| Top Ten Digital City, 3rd (2005), 4th (2006), 6th (2007), 5th (2008), 4th (2009) | Center for Digital Government | 2009 |
| GROA Certificate of Achievement Reporting (30th Consecutive Year) | Government Finance Officers Association of the United States and Canada (GFOA) | 2009 |
| AAA Bond Rating, Moody’s has Ranked City AAA Since 1973, S & P Since 1964 | Moody & Standard & Poors | 2009 |
| Top 10 Healthiest Places to Retire | AARP | 2008 |
| Best Places to Retire, 2nd | Black Enterprise Magazine | 2008 |
| Best City for Living and Launching a Business - 18th Place | Fortune and Money Magazine | 2008 |
| Best Small Market for Business - 9th Place | Forbes Magazine | 2008 |
| 2008 Governor’s Environmental Excellence Award, Gold and Flag Award in the Environmental Program (Government) Category | State of Virginia | 2008 |
| 2008 Bicycle Friendly Community at Silver Level | League of American Bicyclists | 2008 |
| USGBC LEED Gold Certification, Downtown Transit Center, 2008 1st LEED Gold Municipal Designation in the State | USGBC | 2008 |
| One of the Best Places to be Found 1995 & 1999, also one of Seven Dream Towns That Have It All, Best Town to Live 2006, 2008 | Outside Magazine | 2007 |
| Distinctive Designation | National Trust for Historic Preservation | 2007 |
| Environment Excellence Award "Outstanding Achievement for Pollution Prevention Local Government" | Businesses for the Bay | 2007 |
| Best Places to Live | Money Magazine | 2007 |
| Best Small College Town (#1) | E-Podunk.com | 2007 |
| Outstanding Achievement for Pollution Prevention | Chesapeake Bay Stewardship Awards | 2006 |
| Best Trail Running | Outside Magazine | 2006 |
| City Website was Voted, Best City Website - Savvy Award | City County Communications and Marketing Association | 2006 |
| Top Five Green Cities | Blue Ridge Magazine | 2006 |
| Best Place To Relocate | relocateamerica.com | 2006 |
| Best Workplace for Commuters | US Department of Transportation | 2005 |
| Southern Business & Development Magazine: #1 on the List of 10 "Really Cool Small Southern Markets | Southern Business & Development Magazine | 2005 |
| Department of Social Services, USDA Recognition for Outstanding Customer Service | Department of Social Services | 2005 |
| Business Journals - Best Places to Work | Business Journals | 2004 |
| Money Magazine 100 Best Places to Live | Money Magazine | 2004 |
| Awarded First Tee Chapter by the World Golf Foundation | World Golf Foundation | 2004 |
| Best Place to Live in the USA | USA Today | 2001 |
| Best Small Places for Business and Career | Forbes Milken Institute | 1999 |
| Top Ten Places to Retire | Travel 50 & Beyond | Undated |
| #1 State Funded College in America (UVA) | Forbes Magazine | Undated |
| 1 of 10 World Wonders (Monticello and UVA) | National Geographic Traveler | Undated |
| Best College Football Town | Associate Press Readers | Undated |
| 18th Safest Mid Sized Cities in the Country | Farmers Insurance | Undated |
| The Best New Place to Drink Wine | Life Magazine | Undated |
| 10 Perfect Weekend Escapes | Life Magazine | Undated |
| #2 Healthiest Place to Live in America | Kiplinger Magazine | Undated |
| #3 Healthiest Small City to Live in America | Men’s Journal Magazine | Undated |
| Top Ten Places in the Country to Raise a Family | Reader’s Digest | Undated |
| Top Ten Healthiest Cities for Women | American Health Magazine | Undated |
| Best Retirement City for Golfers | Golf Digest | Undated |
| Best Tennis Town | Tennis Magazine | Undated |
| One of the Best Places to Live in America | Arts and Entertainment Television | Undated |
| Most Alive Places to Live | Modern Maturity Magazine | Undated |
| Great Place to Live | Cottage Living Magazine | Undated |
| City Website Received Sponsors Award | National Association of Government Webcasters | Undated |
| City Parks and Recreation Department Recognized as Extraordinary Environmental Enterprise | Virginia Department of Environmental Quality | Undated |
| Tree City USA | Tree City USA | Undated |
| Fire Department - ISO Class 2 Fire Department | ISO | Undated |
