14 Best Small Cities for a First Date

Hayley Matthews

Written by: Hayley Matthews

Hayley Matthews

Hayley has over 10 years of experience overseeing content strategy, social media engagement, and article opportunities. She has also written hundreds of informational and entertaining blog posts. Her work has appeared in numerous publications, including Bustle, Cosmo, the Huffington Post, AskMen, and Entrepreneur. When she's not writing about dating news, relationship advice, or her fantasy love affair with Leonardo DiCaprio, she enjoys listening to The Beatles, watching Harry Potter reruns, and drinking IPAs.

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Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

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Planning a first date is never easy. Do you go casual, or do you go fancy? What activities should you do? Where should you go to eat? It’s nerve-wracking to say the least.

But you know what makes the process a whole lot easier? Being in a great city! (And not just the ones you hear about all the time!)

From cute shops to romantic restaurants to exciting things to do, you can’t go wrong with our 14 Best Small Cities for a First Date, all of which have populations under 230,00.

14. Port Townsend, Washington

What to do: The Olympic Peninsula Wineries, Port Townsend Visual Art Museum and Get Tanked Spa and Boutique

Where to eat: Manresa Castle and Lounge, Fireside Restaurant and Port Townsend Fudge Company.

Where to shop: Getables, About Time Clothing and Earthen Works Gallery

Known as a “Victorian Seaport and Arts Community,” Port Townsend, Washington is beautiful place to have a first date. With numerous cultural events, including festivals, regattas and art walks, you two will never get bored in this seaside city.

13. Asheville, North Carolina

What to do: Biltmore, Addison Farms Vineyard and Grove Arcade

Where to eat: 12 Bones Smokehouse, 5 Walnut and Zambra Tapas

Where to shop: Mast General Store, Malaprop’s Bookstore and Jewels That Dance

As the largest city in Western North Carolina, it would be almost impossible for you and your date to run out of things to do in Asheville, North Carolina. From great music to adrenaline-pumping outdoor activities, romance is around every corner in this charming city.

12. Dayton, Ohio

What to do: Dayton Art Institute, Dayton Dragons Minor League Baseball and Urban Krag Climbing Center

Where to eat: Dewey’s Pizza, Archer’s Tavern and El Meson

Where to shop: The Greene, Austin Landing and Dayton Town and Country

Nicknamed “The Gem City,” Dayton, Ohio truly is a gem for lovebirds. If you’re looking for a first date spot that’s as exciting as this city, then you’ve come to the right place.

11. Healdsburg, California

What to do: Kendall-Jackson Wine Center, Osmosis Day Spa and Healdsburg Museum

Where to eat: The Restaurant at Madrona Manor, Bear Republic and Togos

Where to shop: Healdsburg Shed, One World Fair Trade and Healdsburg Farmers Market

Being one of Northern California’s wine capitals has its perks, and one of those perks is coming in at number 11 on our list. Do you love the outdoors? Can you hold your own on the golf course? Then give Healdsburg, California a chance!

10. Scottsdale, Arizona

What to do: Hot Air Expeditions, MacDonald’s Ranch and Butterfly Wonderland

Where to eat: Sassi, Distrito and J&G Steakhouse

Where to shop: Kierland Commons, Scottsdale Fashion Square and Gainey Village

With the slogan “The West’s Most Western Town,” Scottsdale, Arizona definitely has a lot of personality to it, which makes for an unforgettable first date. Do things you’ve never done, eat foods you’ve never tried and give yourself the best chance at love!

9. New Hope, Pennsylvania

What to do: Triumph Brewing Company, Bucks County Playhouse and New Hope Collective

Where to eat: Marsha Brown, El Tule and Bowman’s Tavern

Where to shop: Heart of Home, Manoff Market Gardens and The Soap Opera Company

Located along the route of the Old York Road, New Hope, Pennsylvania is an adorable city that has equally adorable opportunities for a perfect first date.

8. Coral Gables, Florida

What to do: Riviera Country Club, Bill Cosford Cinema and Fairchild Tropical Botanical Garden

Where to eat: Palme d’Or, Versailles and Christy’s Restaurant

Where to shop: Shop Coral Gables and Village of Merrick Park

Coral Gables, Florida, also known as “The City Beautiful” or simply “The Gables,” is located just southwest of downtown Miami, which means it’s a prime spot for an awesome first date.

7. Pittsboro, North Carolina

What to do: Old Chatham Golf, Carolina Tiger Rescue and Chatham County Historical Museum

Where to eat: The Fearrington House Restaurant, Bella Donna Italian Restaurant and Carolina Brewery and Grill

Where to shop: Fearrington, Cackalacky and Chatham Marketplace

With the nickname “The Circle City,” Pittsboro, North Carolina will have you excitedly circling the city with so many first date options to choose from!

6. Oakhurst, California

What to do: The Madera Vintner Wine Trails, Fresno Flats Museum and The Pines Resort on Bass Lake

Where to eat: Erna’s Elderberry House and The Forks Restaurant

Where to shop: Coarsegold Historic Village

California strikes again, but this time it’s Oakhurst that’s in the spotlight at number six! Take your first date game to the next level in this gorgeous city.

5. Walla Walla, Washington

What to do: Amavi Wine Cellars, Harper Joy Theatre and Walla Walla Symphony

Where to eat: The Marcus Whitman, Brassiere Four and Andrae’s Kitchen

Walla Walla, Washington is such a breathtaking city that they decided to name it twice. Well, you’re sure to be a happy, happy camper after having a first date here!

4. Fredericksburg, Texas

What to do: Lincoln Street Wine and Cigar Bar, Pioneer Museum and Wildseed Farms

Where to eat: Hill Top Cafe, August E’s and The Auslander

Where to shop: Frederick’sburg Herb Farm, Luckenbach Texas General Store and Admiral Nimitz Bookstore

In the heart of Texas lies Fredericksburg, a city any romantic duo will fall in love with. From cigar bars to farms to museums, people go bigger in Texas, and Fredericksburg is no different!

3. Bend, Oregon

What to do: Whitewater rafting, Wanderlust Tours and The Paulina Plunge Downhill Waterfall Mountain Bike Tour

Where to eat: 900 Wall, Bend Brewing Company and Brasada Ranch Farm-to-Table Dining

Where to shop: Goody’s Chocolates, Bend Factory Stores and Cascade Village

It doesn’t matter if you love sports, the outdoors, history or all three — if you want to plan the perfect first date, Bend, Oregon is the place for you.

2. Cambridge, Massachusetts

What to do: The MIT Museum, Charles Riverboat and Cambridge Historical Tours

Where to eat: Park Restaurant and Bar, Russel House Tavern and Temple Bar

Where to shop: MBTA Gifts, Black Ink Boston and The Games People Play

With the nickname “City of Squares,” thanks to most of its commercial districts being major street intersections, Cambridge, Massachusetts is anything but square. The city oozes romance and is filled with spots that were made for first dates.

1. St. Augustine, Florida

What to do: St. Augustine Lighthouse, Ripley’s Believe It Or Not and Fort Matanzas

Where to eat: The Conch House, Saltwater Cowboys and Kingfish Grill

Where to shop: Sandy by the Sea Designs, Sunshine Shop and Wolf’s Head Books

It may also be called “Ancient City” or “Old City,” but don’t let that fool you! St. Augustine, Florida is our number one city for a first date, and for good reason. Go ahead — steal a kiss at the lighthouse or get cozy at one of the fabulous restaurants!

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