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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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