Dorchester County - Heart of the ChesapeakeDorchester County is known as the Heart of the Chesapeake (it’s not only how the county is shaped, it’s who we are!), so it’s a wonderful place to celebrate with your Valentine, whether you’re coming to visit or you live here and you’re staying at home. Here are a few ideas that we’ve gathered for you so you can enjoy this beautiful spot on Maryland’s Eastern Shore!




Hyatt Regency Chesapeake Bay Resort

Hyatt Regency Chesapeake Bay Resort in Cambridge.

Spark romance with a getaway

Plan a getaway and book a room at one of Dorchester County’s quaint B&Bs, hotels, or at the 342-acre Hyatt Regency Chesapeake Bay Resort  with fireplaces to cozy up to, plus treatments at Sago Spa. Reserve at 410-901-1234. Riverside Lodge at Hoopers Island has a quiet and romantic overnight and breakfast package Feb. 11-12. Cambridge House B&B offers a Romantic Package that includes fresh flowers and gourmet chocolates. See more options on our listing of accommodations.


Chocolate and wine pairingThe perfect couple: Wine and chocolate

Indulge in the Wine and Chocolate Pairing (four chocolates, four wines, and a stemless wine glass) at Layton’s Chance Winery Feb. 11 and Feb. 12, 1-2:15pm or 2:30-4pm. Buy tickets.  Or opt for The Chocolate Lovers Affair on Feb. 10 from 6 to 9pm at the ArtBar 2.0, 420B Race St. in Cambridge with a chocolate dessert and wine pairing and live music. More info at 443-988-1554.



Eagle Couple - Photo by Friends of Blackwater

Eagle couple at Blackwater National Wildlife Refuge. Photo courtesy of Friends of Blackwater.

Let your heart soar

Hold hands while you hike with your Valentine on one of the trails at Blackwater National Wildlife Refuge or at Robinson Neck Preserve on Taylors Island. Bring binoculars to see the winter birds. There’s nothing like watching eagles or tundra swans soar through the air! Plus it’s nesting time for eagles! Looking for an easier stroll? Head to Downtown Cambridge, where they have Hearts on Main, with big red, decorated hearts on the lamp posts.


Taqueria Floritas - Valentine special

Boxes with tacos or chocolate-covered strawberries from Taqueria Floritas

Get sweet – or salty!

Pick up sweet delights from these bricks-and-mortar spots:

  • Bay Country Bakery, has Valentine’s specials starting Feb. 11 including  key lime mini bundts, linzer heart cookies, flourless chocolate cakes, heart-shaped meganuts (huge donuts), heart-shaped cakes, and more. Call ahead at 410-228-9111.
  • Black Water Bakery has a Box of Hearts pastry box and pre-date night bubbles & charcuterie board. Order onlineOr customize your own!
  • Cafe Underground has pastries and more.
  • Emily’s Produce has bouquets of their apple cider donuts, along with a handwritten note, hand-delivered to your Valentine. Order by Feb. 13 online.
  • Honey Bee Trading Post has several flavors of caramel hearts as well as honey-inspired sweets, local honey, and more.
  • Mandala Pies has lemon strawberry with chocolate pie as their Valentine’s special in February. By the way, they’re also hosting a Kids in the Kitchen Baking Workshop for beginners Feb. 26.
  • Market at Church Creek has handmade hot cocoa bombs, bacon roses, chocolate platters, chocolate-covered strawberries, cake bites, and more. Open daily through Feb. 14.
  • Simmons Center Market usually has chocolate-covered strawberries and more (call ahead to reserve; 410-228-4313).
  • T’s Divine Sweets & More has pies, cakes, cheesecakes, and cookies. Order ahead at 443-477-6263.
  • Taqueria Floritas is offering heart-shaped boxes with chocolate-covered strawberries – or with tacos! Pre-order one or both by Feb. 9: 443-225-5152. Also, Sweet Tooth Confectionery has a Valentine’s Pop-Up Feb. 12 at 1pm at Taqueria Floritas.

Thomas's Fine Jewelry

Heart of the Chesapeake Dorchester County pendants created by Thomas’s Fine Jewelry

Give a gift from the heart

Find one-of-a-kind and distinctive gifts for your sweetheart in our galleries and independent shops, or consider a gift card. Friendly shopkeepers will help you find a heartfelt gift, whether it’s jewelry, accessories, flowers, or home decor. See a listing of shops. Bay Country Shop hosts Rivers of Love Valentine’s Day Party on Feb. 11 from 10am to 3pm with handmade local jewelry, artwork, and unique gifts. For original art, check out “That ’50s Show” at Main Street Gallery, with 50 works under $50, plus 50% off select pieces. The Dorchester Center for the Arts has a range of works by artists and artisans in their Studioworks shop. And then there are flowers! Check out Flowers N Things (which also has spa baskets and heart-shaped plants) or Florals Unique. Also, Summer Borrelli Photography, based in Dorchester County, is offering a Summers Sweetheart special with 15% off for summer bookings for Valentines. Contact at


Downtown Cambridge - Decorated Hearts

Decorated hearts on lamp posts in Downtown Cambridge. Photo courtesy Blue Awning.

Get dolled up and go out on the town

Add some extra sparkle on Saturday, Feb. 11, when Cambridge Main Street hosts PAL-ENTINE’S Day from 2 to 6pm. Streaming Elegance will be parked at the 400 block of Race Street and performing dry hair services including curls $20, braids $10, and hair extensions (feather, color, glitter): $2 each. Welcome to all ages and genders. Walk-ins subject to availability, for an appointment email There will also be dog treats from Black Water Bakery for your favorite furry friends (while supplies last). It’s also Second Saturday in Downtown Cambridge, with shopping and free gallery receptions at the Main Street Gallery (5-8pm) and Dorchester Center for the Arts (5-7pm). Downtown Cambridge also is sporting decorated hearts on lamp posts.


Entertaining thoughts

Mix it up and grab your Valentine or Palentine for music and dancing or for something a little different…

  • ArtBar 2.0 has SNL Saturday Night Love 7-11pm Feb. 11 with live band, comedy, poetry, DJ. Buy tickets.
  • Blue Ruin in Cambridge has Valentine’s-themed trivia and karaoke on Feb. 14.
  • ArtBar 2.0 has a Dance of Love and Friendship Feb. 18 starting at 6:30pm featuring Mexican snacks and DJ Lobo playing bachata, cumbia, norteño, and salsa. Tickets.
  • Take some fun couple’s selfies at the brand-new POZE Selfie Experience at 437 Race Street. Or stop by 9pm-midnight Feb. 11 for their Galentine’s Day Selfie Party with music, treats, complimentary drinks, and more.
  • Who says axe-throwing isn’t romantic? Or try the virtual escape rooms or golf or shooting simulator at DoCoAxe Co.

Plan for a romantic dinner

Browse Dorchester County’s restaurants and make your reservations. Or bring home some local oysters or crabmeat and create your own romantic evening! See our seafood producers and markets. Some restaurants have announced special Valentine’s menus, and we’ve listed those below. We’ll keep updating this list as restaurants finalize their plans and announce more Valentine’s specials.

  • Blue Ruin in Cambridge has food specials, specialty love cocktails – and Valentine’s-themed trivia and karaoke – all on Feb. 14.
  • Cafe Underground in Cambridge has Valentine’s Day Lovers & Friends Dinner Show Feb. 14, 5:30-8pm with a five-course neo-soul cuisine dinner, wine, champagne toast, and live jazz. Call 443-988-1554 for more info.
  • Emily’s Produce in Cambridge has a three-course Dinner for Two for pick-up or delivery with charcuterie plate, steak and sides, dessert. Order at
  • Johnny’s Tavern has Valentine’s Day specials including filet mignon and crab cake; honey glazed salmon.
  • Millie’s Roadhouse in Vienna has Valentine’s Day specials Feb. 10 and 11 that include frog legs, BBQ bacon wrapped scallops, stuffed oysters, and prime rib. They’re also celebrating their 25th anniversary this month! Call 410-376-3130.
  • Mom -n- Pop’s Restaurant in Hurlock has special Valentine’s menu Feb. 9-11 with prime rib, lobster, and more. Reserve at 410-943-0222.
  • River View at the Point has Valentine’s specials 4-8pm Feb. 10 and 11 including shrimp risotto, prime rib, filet mignon, and more. Free dessert with adult entree. 410-228-0870
  • Suicide Bridge Restaurant in Hurlock has Valentine’s specials Feb. 8-19 including lobster ravioli, champagne salmon, Oscar-style filet mignon, drink specials, and more. (Regular menu also available). On Feb. 14 only, complimentary glass of champagne and chocolate-covered strawberries. Reserve at 410-943-4689.  More info

See all of Dorchester County’s non-chain restaurant options.


Did we miss something? Email us at

Print Friendly, PDF & Email