Updated Feb. 14, 2025

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 or Galentine, 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!

Spark 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 treatments at Sago Spa, and the option to order a package that includes rose petals, chocolate-covered strawberries, and champagne! Reserve at 410-901-1234. See more lodging options on our listing of accommodations.

Valentine's Events

Hearts on Main

Feb. 8
Get into the Valentine spirit with Cambridge Main Street! The fun includes live music by Solitude Road Band at RAR Brewing 6-9pm (the launch of Main Street's new 2025 Second Saturday Music Series), Cupid's Cocktail & Chocolate Crawl at seven participating merchants, and Hearts on Fire with fire pits and s'mores 4-7pm at Blue Ruin Plaza (weather permitting). Plus, personalized hearts will be on display downtown Feb. 8-28.

Family Art Day: Valentine Craft

Feb. 8, 1-3pm
Dorchester Center for the Arts hosts a free, family-friendly arts workshop to create a Valentine craft. All supplies provided.

Valentine's Day Card-Making Workshop

Feb. 8, 1-3pm
Head to Main Street Gallery for this free workshop and dip into artist Robin Morgan's vast collection of stamps. 518 Poplar St., Cambridge.

Seafood Galentine’s Party

Feb. 14, 6-7:30pm

Four Eleven Kitchen at the Packing House hosts a special Galentine’s celebration. Grab your besties and treat yourself to an evening of self-love, sisterhood, and amazing food. Enjoy oyster shucking lessons, mocktails, and small bites. Buy tickets.

Crossroads Community & Corsica River: 40th Anniversary Gala

Feb. 14, 6-10pm
Join in the 40th anniversary Gala with a delicious three-course meal prepared by RAR/Dive Club, beverages, entertainment, silent auction and more – so you can celebrate Valentine's Day with your community. Formal attire is encouraged. At the Packing House in Cambridge. Buy tickets.

Valentine's Day Comedy at Layton's Chance Winery

Feb. 14, 7-8:30pm
An unforgettable night of comedy and good times featuring some of the funniest comedians in the country. This nationwide comedy tour has already made stops at 4500 venues across the country. Buy tickets.

The Oldlywed Game

Feb. 15, doors open 6:30pm; show at 7pm
You've heard of the vintage game show, "The Newlywed Game?" Well, now it's time for "The Oldlywed Game!" Join in for a night of laughs and fun as four couples that have been married 25+ years compete for great prizes. At Old Salty's Restaurant. Tickets cost $5 at the door. Karaoke after the event. Watch for updates on Old Salty's social media.

Eagles at Blackwater National Wildlife Refuge. Photo by Ron Ketter.

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 an eagle or a huge flock of snow geese fly through the air! Blackwater offers free Guided Birding Tours Feb. 9 and 16.

Looking for an easier stroll? Head to Downtown Cambridge, where you can wander the main streets as you browse the shops, explore the art galleries (free art receptions the evening of Feb. 8 at Main Street Gallery, Dorchester Center for the Arts, and 3ten Creative Design & Gift Gallery), stop for a cocktail, and enjoy a meal.

Dorchester County-inspired jewelry at Thomas's Fine Jewelry. Photo courtesy Thomas's.

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 has Simply Southern Valentine's Day items 50% off.
For original art, check out "All That Glitters: A Metalsmith Collective" at Main Street Gallery, with jewelry and more. You'll find more original art at the StudioWorks store at the Dorchester Center for the Arts and at 3ten Creative Design & Gift Gallery. And then there are flowers! Check out specials at Flowers N Things or Florals Unique (this year's special features flowers arranged in a Buc-ee's Valentine's cup or the Stanley Valentine cup), Rebecca's Roses -n- Brianna's Bows (Hurlock) or the Market at Church Creek.

Chocolate-covered strawberries at Market at Church Creek. Photo courtesy Market at Church Creek.

Get sweet

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

• All kinds of handmade treats, from chocolate-covered strawberries to 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.
• 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.
• 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).

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 serves up a special Valentine's menu Feb. 14 and 15 with decadent appetizers (lobster bisque, oysters), luxurious main courses (from duck confit ravioli to filet mignon), sweet desserts, and a complimentary champagne toast. Vegetarian friendly. See menu on their social media. Reserve at 410-995-7559 or online.

• Old Salty’s Restaurant has Valentine specials Feb. 12-16 including soft crab nuggets, filet mignon, and stuffed shrimp. Reserve at 410-397-3752.

• Suicide Bridge Restaurant has Valentine's specials available through Sunday, Feb. 16, including lobster ravioli, filet mignon with lobster cream, rockfish oscar, veal chop, and more. Reserve at 410-943-4689.
• The Hyatt Regency Chesapeake Bay has a Valentine's Day Dinner Feb. 14, 5-9pm with a specially curated three-course Valentine's Day menu featuring coastal flavors, a decadent dessert, and the option to share a bottle of house-selected wine. $65 per person (+$30 for wine). Reserve at 410-901-1234.
• Mom - N - Pop's in Hurlock is offering Valentine's specials including surf and turf, spare ribs, pork chops, salmon, and more. Feb. 13-15, 5-8pm.
• Ava's Pizzeria is serving heart-shaped pizzas Thursday, Feb. 13 through Sunday, Feb. 16.
• Emily’s Produce is officially closed for the winter season, but they're offering a special Valentine's  dinner for two. It includes local Delmonico steaks ready for cooking, cheesy scalloped potatoes, roasted veggie medley, sweet potato biscuits, and blackberry lemon streusel pie. Plus a dried wildflower bouquet. Add-ons include a bottle of local wine or a local charcuterie assortment. Place your orders at emilysproduceorders.com. Available for pick-up or delivery.

For more restaurant options, see our Dorchester Dining Guide.

Have something to add? Email us at jill@visitdorchester.org.