45-Plus Creative Dates to Go on in Delaware This Fall and Winter

Need some fun, fresh ways to woo your significant other? Look no further.


Need to find a fresh, fun new way to woo your significant other this fall and winter? Delaware has all you need for seasonal romance.

Sydney Kerelo, Mark Nardone, Brooke Schultz and Danielle Bouchat-Friedman contributed to this article. 

As the weather starts to turn cold, the skies get drearier and the days get shorter, it can be hard to date someone new while battling seasonal depression. Well, we have some ideas to do just that!

Here are 45 ways to get to know someone, from low-key and casual to epic and romantic.

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1. Take a walk on the beach. Yes, it’s October. Yes, it’s a bit chilly. Yes, the beaches can seem desolate, especially at the state parks. But they are beautiful, you’ll be alone, and, afterward, both of you will be in need of warmth.

2. Meet for coffee or hot chocolate. Brew HaHa! serves at locations across New Castle County—and some have cozy fireplaces. Geek on exotic varietals and pour-over service at Drip Café in Hockessin or Newark.


3. Enjoy an oyster happy hour at Harry’s Savoy Grill in Wilmington. On Sundays, you can enjoy the classic course, which serves a delicious prime rib, clam chowder soup and more. Other favorites: Trolley Square Oyster House in Wilmington, the Big Fish Grills upstate and down, and Blue Coast Seafood Grill, Fins Fish House and Henlopen City Oyster House at the beaches. And that’s just the start. Need we say more?

4. Add a twist to the classic dinner-and-a-movie date. See a foreign film at intimate Theatre N at Nemours in Wilmington, which shows first-run indie and foreign films. The Cinema Art Theater in Lewes offers more of the same, plus live broadcasts of Broadway shows and performances of the Metropolitan Opera and plays from the National Theatre in London.

5. Ponder the mysteries of love and the universe during a garden highlights tour at Mt. Cuba in Greenville. Nothing inspires awe more than a look at the nature that surrounds you.


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6. Make a night of the theater at The Candlelight Theatre Delaware, where each main stage production comes with a meal. This month takes a look at “The Best of Candlelight,” but things turn cheerful with “A Christmas Carol at Candlelight” in December. At Delaware Theatre Company, enjoy “Tommy and Me” or listen to the musical styling of Elvis Presley in “Million Dollar Quartet.”

7. Try climbing the walls at Delaware Rock Gym in Bear. Climb free on the bouldering wall, which features tricky overhanging “problems.” Or take a lesson in belay—arresting your falls—on the vertical routes (you’ll be harnessed and roped). You’ll soon find out which of you has trust issues…

8. Go dancing with your star during a ballroom class. You may feel like a clod at the start, but you’ll feel confident and sexy at the end. Check the schedule at BlueBallRoom in Wilmington or Take the Lead Dance Studio in Hockessin.

9. Volunteer. Tapping into your shared philanthropic values is a good way to get to know your date while giving back. Deliver Meals on Wheels or walk dogs together for the Delaware SPCA. Tutor a kid. Clean up a stream. Plant dune grass at the beach or count horseshoe crabs. Drive a senior to the doctor. Coach a mock-trial team. There are dozens of organizations with diverse missions that are looking for you. Check the membership of the Delaware Association for the Advancement of Nonprofits at delawarenonprofit.org, then call your fave.

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10. Make sweet music during a chamber concert. Delaware Symphony Orchestra continues its chamber series with “Quattro Staggioni (Four Seasons),” featuring Concertmaster David Southorn, at the DuPont Country Club on November 16.

11. Clink glasses together. A glass of a local beer or bourbon will quell any first-date jitters. Which to sample? And where? Consult the Delaware Beer, Wine and Spirits Trail. You’ll find more than 30 places with tasting rooms where you can savor the best in craft brewing, distilling and more. Newish to the trail: a cidery and meadery. Cheers.

12. Go antiquing. Delaware and the Brandywine Valley are among the oldest parts of the United States, and that history means there are many vintage pieces to be found. You can spend any afternoon scouring local antiques and collectibles stores, or you can visit Winterthur Museum, Garden and Library’s Delaware Antiques Show each November.

13. There would be no flowers without birds and bees—which makes Longwood Gardens an ideal place for love to blossom. There is no nook of the sprawling outdoor gardens or famous conservatory that is not beautifully romantic. During your visit, save room for a delicious dinner in 1906 or a casual cup in the café. Indoor and outdoor venues stage plays and concerts from raga to jazz to classical by national and international talents. Take a class in flower arranging together. Or attend one of those spectacular fountain shows.


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14. Stroll Winterthur Museum, Garden and Library. The galleries of American decorative arts are fascinating, the gardens are world-class, and the house will leave you feeling all Gatsby and Daisy.

15. Become enthralled in the favorite holiday tradition, “The Nutcracker,” performed by the First State Ballet Theatre. Experience the magical journey firsthand as Delaware’s only professional dance company brings to life the land of sweets on Dec. 10-12.

16. If dating isn’t scary enough, take a ghost tour or experience life during the Civil War at places like Fort Delaware and towns such as Lewes, where the history runs deep. October brings a surfeit of spooky fun during tours of historic properties such as the Rockwood Mansion.  

17. Trains have a romance all their own, so ride in a vintage coach on the Wilmington & Western Railroad. Start at Greenbank Station, roll through the beautiful Red Clay Valley, then stop in Hockessin to purchase a dinner to eat during the return trip. Check the dinner train schedule at wwrr.com.

18. Cooking together is a hands-on way to get to know one another. Take a class at Chefs’ Haven in Hockessin.

19. Visit a winery. They are, by definition, intimate. Visit Nassau Valley Vineyards, in Lewes for a self-guided tour of the vineyards or a taste of its delicious chardonnay. Salted Vines Vineyards in Frankford has a wide array of wines from Pinot Grigio to Blackwater Red. Or do a wine tasting at Delaware’s four vineyards—Harvest Ridge, Pizzadili, Nassau Valley and Salted Vines—since all have tasting rooms, or head north on the Brandywine Valley Wine Trail.

20. Go on a picnic. Grab delicious food from a place such as Toscana to Go in Wilmington or Lewes Gourmet, then head to a favorite outdoor area. Spread your blanket near the ponds at Carousel County Park in Pike Creek, under the cliff at Alapocas Run State Park or next to an isolated stretch of the Broadkill at McCabe Preserve near Milton.

21. Visit an art museum. We are fortunate to have several good ones. Viewing the Pre-Raphaelite works at Delaware Art Museum is a window to the romances between famous painters and their models. Peek through the lens of photographer Nickolas Muray with his portraits of Frida Kahlo at the Biggs Museum of American Art.

22. If you don’t take yourself too seriously (or if you’ve been told you sound just like Marc Cohn when you belt out “Walking in Memphis”), a host of bars and restaurants feature karaoke nights, including 1984, Catherine Rooney’s, the Golden Fleece Tavern in Dover and more.

23. Plant a garden together. Whether you reap the harvest as a couple may remain to be seen, and we’ll skip transparent metaphors about nurturing life, but you might as well sow the seeds. Apply for a plot at Bellevue Farms. Or bring a date along while you help in a community garden managed by The Delaware Center for Horticulture.

24. You can learn a lot about relationships through horses, so take a lesson together. Facilities such as Sunset Stable in Bear offer classes and opportunities such as one-hour trail rides at Lums Pond.

25. Float in a hot air balloon. You’ll have a truly panoramic view of the countryside when you fly with outfits such as Delmarva Balloon Rides in Chester, Maryland. It’s peaceful, exhilarating and inspiring. You’ll be a hero.

26. Rock out. If you both love loud music, there are several venues that can oblige. Hit the Bottle & Cork in Dewey Beach and The Queen in Wilmington for big regional and national acts, such as Veronica Lewis on Nov. 11. For local bands and a bit more edge, hit Bar XIII in Wilmington.

27. Mellow out—kind of. For live music in a mellower setting, visit a cozier bar, such as The Nomad in Wilmington, Nora Lee’s French Quarter Bistro in New Castle or St. Georges Country Store for great jazz and blues. Home Grown Café in Newark hosts great pop and rock groups.

28. Play tourist. No matter where you live or visit often, everything will seem new to someone who has never seen it before. So on a date, it will look brand new to you, too. One place to play tourist is in Historic New Castle, the scene of many a date and marriage proposal.

29. Tour Colonial properties such as the George Read House and Garden, wander through the grounds of Immanuel on the Green Church and amble along the shores of the Delaware River in Battery Park. Successful afternoon? Dine by the fireplace at Jessop’s Tavern. 

30. Go for the thrills when you ride the Go Ape! zip line at Lums Pond. Harness up, then tiptoe through the trees and zoom along a steel cable. If your date hasn’t been scared off, repair to St. Georges Country Store. (See No. 27.)

31. Cruise the Cape May-Lewes Ferry across Delaware Bay. Park at the terminal, then walk on for a round trip of just over three hours. On board, enjoy a drink as you sail. Summer brings live music, wine and beer events, and more adult fun. The breezes are fabulous. The sunset views are amazing. Make sure you time it right.

32. Go to an escape room. You have one hour to find the key that lets you out. Work together to solve the clues in rooms built on themes such as a paper company in Scranton and Shawshank Prison and in a galaxy far away. Locations include Great Escape in Newark and Novus Escape Room in Middletown.

33. Who says a first date needs to be a dinner date? Plan a Sunday meet-up at a favorite brunch spot. You’ll be charmed by the intimate nature of the Back Porch Café in Rehoboth Beach or the Victorian-ness—and the ocean view—at Victoria’s Restaurant in Rehoboth Beach.

34. Tap into your creative sides at Painting With a Twist. Following the instruction of an artist, you can create a memento of your time together. On scheduled date nights, you paint one half of the image, your date paints the other. Visit either the Wilmington or Newark locations and paint with your choice of wine for $44.

35. Laugh. Hit a comedy show. Guy Torry and friends visit the House of Laffs on Nov. 19 & 20, and six-time Emmy award winner Louis CK will perform his standup comedy at The Grand on Nov. 2.

36. Visit OperaDelaware’s studios on the Wilmington Riverfront for intimate events such as the Sunday Spotlight featuring recitals by Jennifer Zetlan and Aurelien Eulert on Dec. 5.

37. Book a Swedish massage or classic pedicure at The Spa at Montchanin Village, one of the most luxurious spas around. (Tip: Do not book a facial. She will not want to have to redo her makeup afterward.) Then enjoy a meal at whimsical Krazy Kat’s.

38. Test your collective knowledge of trivia with a few rounds of beer and Quizzo, a popular bar game. Pubs such as Gallucio’s and Chelsea Tavern in Wilmington host weekly trivia nights that are perfect for a low-key group date or a one-on-one showdown.

39. Leave your dress shoes and heels at home and rent some bowling shoes. There are at least a dozen alleys from which to choose. Bowlero in Wilmington hosts Monday Mayhem after 9 p.m., during which time guests get a discount on prices, free shoe rentals and more. Lefty’s Alley & Eats in Lewes has 16 bowling lanes, with bowling available for $20 per hour. Plus, get excited for delicious craft cocktails and chef-inspired foods.

40. Sample a new flavor of pizza that you both have never tried before.

41. Run a 5K—and get free beer. There’s nothing like trying to impress your date with your athletic abilities. (Just make sure you’re up to the challenge.) There are special races and race series up and down the state year round, but the Turkey Day 5K Run/Walk in Camden Wyoming on Nov. 25 gives back to the community with food donations to The Shepherds Place Family Shelter. 

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42. This winter take your beloved on a trip to a ski resort. There are three ski areas less than two hours from Wilmington—Spring Mountain, Bear Creek and Blue Mountain, all off I-476 in Pennsylvania—where you can take lessons in skiing or snowboarding. Skip the group class. You’ll pay extra for a private instruction, but this is a date after all—and not a competition.

43. Live your own “Love Story.” Although The Riverfront Rink in Wilmington is closed this season due to COVID-19 precautions, the Skating Club of Wilmington is the next best thing. It’s open every Wednesday, Friday, Saturday and Sunday. You can also break the ice during Public Skate at The Patriot Ice Center in Newark or during sessions at the Fred Rust Ice Arena at the University of Delaware, The Skating Club of Wilmington or the Centre Ice Rink in Harrington.

44. Too cold for the ice? Try roller-skating. If you haven’t been since you were a kid, enjoy Friday and Saturday night skating sessions at the Christiana Skating Center for only $8 per person. Open skate sessions at Dover Skating Center happen on Saturday and Sunday afternoons. Keep it low-key.

45. Show your playful side and go sledding. Hit Bear Mountain at Glasgow Regional Park, brave the steeps at Brandywine Creek or White Clay Creek state parks, or schuss at Rockford Park, the epicenter of snow-day fun in Wilmington. After, see No. 2.

46. Watch a sunset. All you need is an open horizon.

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