Dorchester 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 ResortSpark some 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 holiday-themed treatments at Sago Spa, and love-inspired recreational activities for guests. Reserve at 410-901-1234. Riverside Lodge at Hoopers Island is offering a limited number of all-inclusive experiences with a three-course candleit dinner, champagne toast, brunch, and overnight accommodations. 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. 12 and Feb. 13, 2-3:15pm or 3:30-5pm. Buy tickets.  Or opt for The Chocolate Lovers Affair on Feb. 11 from 6 to 9pm at the new ArtBar 2.0, 420B Race St. in Cambridge with a chocolate dessert and wine pairing and live music. Buy tickets.


Jazzy Valentine'sGo jazzy

Get in the swing with the Jazzy Valentine’s Concert Feb. 12 at 7pm featuring “Songs of Love and Happiness” with Linda Harris and Felipe Paccagnella at the Dorchester Center for the Arts. Buy tickets.



Eagles at Blackwater National Wildlife Refuge - photo by Lisa MayoLet 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 an eagle or a huge flock of snow geese fly through the air! Looking for an easier stroll? Head to Downtown Cambridge, where they have Hearts on Main, with big red hearts on the lamp posts, each with hand-painted personal messages of love. Hearts will be installed in early February and stay up until the end of the month. See the hearts on the 300 block of High Street, the 400 block of Race Street, and the 500 block of Race Street. (And if you want to try something really different for your date night, head to the DoCo Axe Co. for some axe throwing!)


Chocolate covered strawberriesGet sweet

Pick up treats from these bricks-and-mortar spots:

  • Salted caramels, fudge, hot cocoa bombs, bacon roses (made with real bacon!) and more at the Market at Church Creek (pre-orders recommended).
  • Valentine’s-themed cookies and other goodies from Black Water Bakery. Or customize your own!
  • Simmons Center Market 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.
  • All kinds of freshly baked goods at Bay Country Bakery, including Valentine-themed cakes, cookies, and meganuts (huge donuts) (best to call ahead; 410-228-9111).
  • Emily’s Produce has chocolate-covered wine bottles, hot cocoa bombs, and other treats that you order online and pick up at the market. (The market is otherwise closed for the winter.)
  • The new Cafe Underground hopes to open in early February with pastries and more. 420 Race St. in Cambridge. Check their Facebook page for the latest.

Thomas's Fine JewelryGive 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. 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 “Black History Past and Now” starting Feb. 4, featuring quilts by the Brown Quilters Create and Educate Group. Layton’s Chance Winery is offering to help you create a custom gift basket Feb. 10 from 5 to 7pm. And then there are flowers! Check out Flowers N Things or Florals Unique or the DCTC (Dorchester Career & Technology Center) Greenhouse.


Plan for a romantic dinner

Browse Dorchester County’s restaurants and make your reservations or plan for a to-go feast. 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 has 15% off bottles of wine Feb. 11, 12, and 13. Plus plenty of Valentine’s desserts and drinks available.
  • Bombay Social is open on Valentine’s Day itself (Monday, Feb. 14) with a four-course tasting vegetarian and non-veg menu; pair it with their special Valentine’s cocktail. Reserve at 443-515-0853.
  • Emily’s Produce has a Valentine’s Day dinner bundle featuring steaks that you order online and pick up at the market or have delivered. (The market is otherwise closed for the winter.)
  • Fat Ricky’s is  offering a Valentine’s dinner for two on Feb. 14, 5-9pm, featuring ribeye, lobster tail, sides, dessert, and a complementary bottle of champagne. Plus other Valentine’s specials, too. Reserve at 443-382-0257.
  • Jimmie & Sook’s has a special Valentine’s menu Feb. 11 and 12 with appetizers such as lobster bisque and an oyster trio, entrees including surf and turf and house smoked brisket, desserts such as chocolate lava cake and more. Regular menu also available. Reserve at 410-228-0008.
  • Johnny’s Tavern has Sweetheart Specials Feb. 12 from 5 to 9pm with a 24-oz. heart-shaped ribeye steak to share, lobster tails for two, and more. Reserve at 410-943-3624.
  • Maryland Blue has a Valentine’s menu that includes oysters Rockefeller, seared scallops, filet mignon, and more. Regular menu also available.
  • Millie’s Roadhouse has a special Valentine’s menu with appetizers such as frog legs and oysters casino, and entrees including shrimp and scallops, stuffed soft shell crabs, prime rib, and more. Reserve at 410-376-3130.
  • Mom N Pop’s has a Valentine’s menu with a dinner for two featuring  steak and crab cake and more; plus other dishes ranging from oysters topped with crab imperial to a seafood combo. Reserve at 410-943-0222.
  • Old Salty’s has a set Valentine’s menu on Saturday, Feb. 12 that includes crab cakes, steak, prime rib, local perch, shrimp, and more. See the menu. Reserve at 410-397-3752.
  • Snapper’s Waterfront Cafe goes for rockin’ good fun with the Agitators performing starting at 8pm on Feb. 12. Reserve at 410-228-0112.
  • Suicide Bridge Restaurant has specials for on-site dining Feb. 9-20 including whole Maine lobster, rockfish, and steak dishes. (Regular menu also available). On Feb. 14 only, complimentary glass of champagne and chocolate-covered strawberries. Reserve at 410-943-4689.  More info
  • Theo’s Cambridge is open Monday, Feb. 14. Reserve at
  • Vintage 414 is offering a 3-course to-go Valentine’s Dinner with scallops and shrimp pot pie for Feb. 13; order by 12pm Feb. 9. Their menu includes suggested wine pairings. More info
  • Water’s Edge Grill at the Hyatt Chesapeake offers a special four-course Valentine’s dinner Feb. 11 and Feb. 12 between 5:30pm and 9pm. Entrees include a beef filet, a salmon dish topped with a black garlic sauce, and a duck breast. Reserve at 410-901-6400.

For more restaurant options, see our Dorchester County Eats Guide.


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