The 2019 Ultimate Guide to Great Dates in Delaware

From low-key and casual to creative and offbeat, here are 47 ways to get to know someone else.



Head for the mountains. 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.


Live your own “Love Story.” When the mood is right, The Riverfront Rink in Wilmington can feel like Wollman Rink in Central Park. It’s open seven days a week through winter. You can also break the ice at public skating sessions at the Fred Rust Ice Area at the University of Delaware, The Skating Club of Wilmington or the Centre Ice Rink in Harrington.

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


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.


Take a walk on the beach during the more peaceful off-season. 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.


Break the ice at the Riverfront Rink in Wilmington.//photos by Joe Del Tufo, Moonloop Photography

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Meet for coffee or hot chocolate. Brew HaHa! serves both 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 go French. Café Papillon in Rehoboth and De La Coeur Café et Pâtisserie in Wilmington offer hot chocolate and pastries that make delicious first impressions.


Enjoy an oyster happy hour at Banks Seafood Kitchen on Wilmington’s Riverfront. Other favorites: Trolley Square Oyster House in Wilmington, the Big Fish Grills upstate and down, and Blue Coast Seafood GrillFins Fish HouseHenlopen City Oyster House at the beaches. And that’s just the start. Need we say more?


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.


Dine by the fireplace at Dilworthtown Inn. The setting is historic. The food is fabulous. The wine selection is amazing. The experience is peerless. More than 200 years’ worth of guests can’t be wrong.

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Ponder the mysteries of love and the universe during a stargazing night at Mt. Cuba in Greenville. Nothing inspires awe more than a look at the sky guided by a professional astronomer. Visit a public night at the observatory through the cold months. When the weather warms, gaze from the lawn. Don’t forget to say hello to Venus.





Make a night of the theater. The Candlelight Theatre, is where each main stage production comes with a meal. The legendary theater is celebrating its 50th anniversary this year. Delaware Theatre Company along Wilmington’s Riverfront is another fine choice.


Is life driving you up a wall? Try it 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…


Eat chocolate. Visit the annual Rehoboth Beach Chocolate Festival in March. Sample decadent and amazing creations from local restaurants and stores, and feel good about supporting charities. If you want to show up for your date with a box, shop at the iconic Govatos Chocolates in Wilmington.


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, Take the Lead Dance Studio in HockessinStarliters Dance Studio in Wilmington and more.


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, then call your fave.


Clink glasses together at tasting rooms across the state.



Make sweet music during a chamber concert. Brandywine Baroque presents concerts of English and French music. Delaware Symphony Orchestra continues its unparalleled performances. Check the websites for local concerts by Mélomanie, Pyxis Piano Quartet and Serafin String Quartet.


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, vinting, distilling— even a cidery and meadery or two. Cheers.


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 special events such as the Brandywine River Museum of Art Antique Show every Memorial Day weekend and Winterthur Museum, Garden and Library’s Delaware Antiques Show each November.


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..


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.


Stroll one of the popular gardens at Winterthur, Longwood or the Nemours Estate.//photo by Joe Del Tufo, Moonloop Photography



If dating isn’t scary enough, take a ghost tour. There are opportunities year round at places like Fort Delaware and towns such as Lewes, where the Lewes Legends Tour introduces a bit of the ghost stories that attend the town’s founding. But October brings a surfeit of spooky fun during events such as Dark Dover Lantern Tours, and tours of historic properties such as Rockwood Mansion and Bellevue Hall.


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 for dinner, where you’ll dine at the Back Burner restaurant before the return trip. Check the dinner train schedule at


Cooking together is a hands-on way to get to know one another. Take a class at Chefs’ Haven in HockessinSoDel Concepts at the beach offers regular cooking demos at several of its popular restaurants such as NorthEast Seafood Kitchen.


Visit a wine bar. They are, by definition, intimate. Domaine Hudson in Wilmington holds special date nights. Or visit any night of the week, take a seat at the cozy bar, then get close while you view the list of 450 bottles on the iPad.


Do a wine tasting. Delaware’s four vineyards—Harvest Ridge, Pizzadili, Nassau Valley and Salted Vines—all have tasting rooms, as well as special events such as Harvest Ridge’s food truck and music nights. Or head north on the Brandywine Valley Wine Trail. Warmer weather brings concerts, outdoor movie nights, craft fairs and more at member vineyards. You never know—you could be subconsciously scouting a reception site…


Spread a blanket and chill at one of the state’s beautiful parks.//photo by Joe Del Tufo, Moonloop Photography



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, next to an isolated stretch of the Broadkill at McCabe Preserve near Milton, or on the banks of Silver Lake in Dover.


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. The landscapes of Hudson Valley School painters at the Biggs Museum of American Art in Dover will transport you both to a different time and breath-taking places. The Wyeth family art at the Brandywine River Museum of Art is stunning, and the view of the creek makes the café a charming place for a cup and a chat.


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 1984Catherine Rooney’s, the Golden Fleece Tavern in Dover, the Blue Moon and Purple Parrot Grill, both in Rehoboth—and plenty more.


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 State Park. Or bring a date along while you help in a community garden managed by The Delaware Center for Horticulture.


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.


Horse riding lessons can make for a romantic afternoon



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.


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 Blues Traveler on Feb. 22. For local bands and a bit more edge, hit Bar XIII in Wilmington. Or buy an extra ticket soon for the Firefly Music Festival in June. You can worry about whom to take later.


Mellow out—kind of. For live music in a mellower setting, visit a cozier bar, such as The Nomad in WilmingtonNora 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. Grey Hare Tavern in Rehoboth Beach offers rock and blues. And The Metro Pub & Grill in Middletown promises a fun Friday and Saturday night.

34. Play tourist. No matter where you live or visit often, everything will seem brand new to someone who has never seen it before. So on a date, it will look brand new to you, too.



Play tourist in Historic New Castle, the scene of many a date and marriage proposal. Tour Colonial properties such as the George Read House and Garden, wander through the grounds of Immanuel on the Green Church, browse quaint shops such as HedgeApple Antiques on Delaware Street and amble along the shores of the Delaware River in Battery Park. Successful afternoon? Dine by the fireplace at Jessop’s Tavern. Or buy a ticket for A Day in Old New Castle in May to get an inside look at a few fantastic homes and gardens.


Do a wine tasting—or sneak away for a minute—at one of the local vineyards’ tasting rooms.//photo by Jim Coarse, Moonloop Photography



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.


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.


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 Shawshank Prison and “National Treasure.” Locations include Exodus Escape Room in Newark, Wilmington and Rehoboth Beach, Great Escape in Newark and Escape Room Delaware in Dover.


Who says a first date need be a dinner date? Plan a Sunday meet-up at a favorite brunch spot. You’ll be charmed by the Frenchness of tiny De La Coeur Café in Wilmington and the Victorian-ness—and the ocean view—at Victoria’s Restaurant in Rehoboth Beach.


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 any of the four studios—Wilmington, Newark, Middletown and Lewes—and paint with your choice of wine for $40.


Catch a romantic sunset over one of the inland bays.//photo by Joe Del Tufo, Moonloop Photography


41. Laugh. Hit a comedy show at The Playhouse on Rodney SquareThe Grand Opera House or the Milton Theatre, which hosts a variety of comics.


42. Visit OperaDelaware’s studios on the Wilmington Riverfront for intimate events.




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.


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 or Grain in Newark host weekly trivia nights that are perfect for a low-key group date or a one-on-one showdown. Downstate, try Let’s Do Trivia live at Grotto Pizza or Arena’s.


Leave your dress shoes and heels at home and rent some bowling shoes. There are at least a dozen alleys to choose from. First State Lanes in Wilmington, Brunswick Zone Doverama Lanes and Lefty’s Alley & Eats in Lewes.


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.

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


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