Romantic May Date Adventures for Engaged Couples in Carroll County, MD

Date Night in Carroll County, Maryland

Today’s blog is about dates engaged couples can do in the month of May in Carroll County, Maryland.  As the owner of Montagu Meadows, a barn wedding venue in Westminster, Maryland, May is a very busy wedding month.  My husband and I try to take some time during the week and a wedding free weekend free to do something fun.  And May is the perfect time to do this. May is a magical time to be engaged or just a couple in Carroll County, Maryland. The flowers are in full bloom, the weather is just right, and the calendar is packed with indoor and outdoor events perfect for couples ready to celebrate their love. Whether you’re looking for lively festivals, intimate vineyard dates, or historic adventures, Carroll County has endless options to make your spring unforgettable. Here’s your guide to the best May date adventures for engaged couples:

Sip, Savor, and Celebrate Love in Carroll County, Maryland

Carroll County’s vibrant wine and brewery scene is expanding and is perfect for couples who want to relax and toast to their future together. Kick off your May with a visit to:

Serpent Ridge Vineyard located in Westminster, Maryland

                •             Old Westminster Winery – Lounge in the sunshine, sip handcrafted wines, and enjoy wood-fired pizzas on their beautiful farm.

                •             Galloping Goose Vineyard and Serpent Ridge Vineyard – Both

offer peaceful, romantic settings to share a glass (or a bottle!) while soaking in Carroll’s stunning countryside and sunsets.

                •             Pub Dog Brewing Company – Fun and casual, perfect for a low-key afternoon date with pizza and craft brews.

                •             Johansson’s Dining House & Brewery in Westminster – Cozy up over house-made beers and a delicious dinner.

                •             Covalent Spirits – For couples who appreciate craft cocktails and locally distilled spirits.

                •             Brewery Fire, Flood Zone Brewery, 1623 Brewing Company– Breweries all across the county offer unique brews, live music, and fun atmospheres to enjoy a relaxed, laughter-filled date.

Celebrate at Festivals and Events in Carroll County, Maryland

May in Carroll County is all about festivals — and they make for some of the best engaged couple dates:

                •             Sykesville Art and Wine Festival (May 3, 2025) – Stroll historic Main Street, tasting local wines and browsing unique art pieces. It’s the perfect blend of culture and romance.

                •             Westminster Flower and Jazz Festival (May 10, 2025) – Enjoy jazz performances, endless flowers, and shopping, creating the ultimate springtime date vibe. 

                •             55th Annual Flower and Plant Market at Union Mills Homestead (May 10-11, 2025) – A dreamy spot for couples who love gardening or want to pick out flowers together for their future home.

                •             51st Annual Hampstead Day (May 17, 2025) – A day filled with food, crafts, and live entertainment—ideal for a playful and nostalgic afternoon date

                •             Westminster Memorial Day Parade (May 26, 2025) – Cap off the month by watching one of Maryland’s most beloved Memorial Day parades hand-in-hand with your fiancé(e).

And for an unforgettable night out, Jazz Night at WMC Alumni Hall offers smooth tunes and a sophisticated setting for a romantic evening.

If you’re in the mood for a little more edge and humor, grab tickets for John Waters: The Naked Truth — a hilarious storytelling night that’s sure to spark conversation and lots of laughs.

Walk Through History Together in Carroll County, Maryland

For couples who are history buffs, Carroll County offers Civil War walking and driving tours that take you through historic battlefields, preserved towns, and scenic backroads. It’s a unique way to bond, learn, and reflect on the shared history of the region. Plus, it’s a beautiful excuse to spend a day adventuring outdoors.

Outdoor Romance

If you want to keep it simple and sweet, take a day to hike together at Piney Run

Piney Run Park located in Carroll County, Maryland

Park, Bear Branch Nature Center, or explore Patapsco Valley State Park. You can also plan a romantic picnic at Hashawha Environmental Center filled with local treats and a bottle of wine from your earlier vineyard visits!

Make It a May to Remember

Carroll County truly shines in May, offering everything an engaged couple could want: romance, adventure, laughter, stunning landscapes and a little bit of magic. Whether you’re dancing at a jazz festival, sipping wine under the stars, or exploring historic streets, each date is a new memory to cherish on your journey toward “I do.”

So grab your fiancé, plan a few weekend adventures, and fall even more in love this May in Carroll County, Maryland. You will not regret it. Time together is precious!

Our History, Your Love Story – Montagu Meadows, an Historic Barn Wedding Venue in Westminster, MD

Montagu Meadows - a stunning barn wedding venue located in Westminster, MD

Looking for a stunning affordable Maryland barn wedding venue? Consider touring the Historic Montagu Meadows Wedding Venue located in the countryside of Carroll County, MD.  Montagu Meadows offers full-size dream weddings with receptions and intimate/elopement packages. Our wedding

venue offers a breathtaking setting with a team dedicated to making your wedding day perfect. Montagu Meadows has stunning gardens and serene water views, creating a picturesque backdrop for unforgettable celebrations.  We also proudly support the LGBTQ couples in a warm, inclusive environment.  If you are looking for an elegant, rustic, and unforgettable wedding that is pet-friendly, contact us to schedule a tour. 

Visit our Website: www.montagumeadows.com

Visit our gallery for additional photos: GALLERY | Montagu Meadows

Visit our intimate wedding ceremony page for package options: ELOPEMENT & INTIMATE WEDDINGS | Montagu Meadows

Email us at: crkrone46@gmail.com

Location: Westminster, MD in Carroll County

Montagu Meadows happily serves the entire Carroll County, Maryland area which includes Sykesville, Eldersburg, Woodbine, Mount Airy, Taneytown, New Windsor, Union Bridge, Westminster, Manchester, Hampstead, and Lineboro.  We also serve other Maryland Counties:  Anne Arundel, Howard, Frederick, Baltimore, Baltimore City, Harford, Montgomery, Prince George’s and Washington and along with Southern Pennsylvania which includes Adams, Lancaster, Franklin and York Counties.

Thank you for reading our blog.  We hope you find inspiration and helpful advice in all our wedding blog posts. Contact us today to start planning your dream wedding and discover how Montagu Meadows can transform your special day into a warm, timeless celebration!

We are dedicated to using our platform to support locally owned wedding venues.  In every blog we write, we will give a shout out to other independently owned wedding venue owners around the country that offer their support and encouragement on a daily basis:

 The Old Barns at Dry Run

The Bella Rosa

 The Notting Hill Farm