
As the owner of Montagu Meadows, a Maryland barn wedding venue since 2017, I have met a lot of wonderful, engaged couples who enjoy telling me about their proposals. I always find it interesting how they plan and where they executed their proposal. Planning a proposal in Maryland is an exciting journey, but it also comes with a lot of moving pieces and some stress. Valentine’s Day is the ultimate celebration of love, making it the perfect time to take your relationship to the next level. Valentine’s Day is the perfect day to do it. Maryland, with its mix of scenic landscapes, charming towns, and romantic venues, offers endless possibilities for a memorable proposal. Whether you want a grand gesture or an intimate moment, here are five romantic ways to pop the question this Valentine’s Day in Maryland:
1. A Scenic Waterfront Proposal in Annapolis or St. Michaels
Annapolis, Maryland’s historic capital, provides a picturesque backdrop for a proposal. Known for its charming cobblestone streets and beautiful views of the Chesapeake Bay, it’s the perfect spot for a romantic outing. Start with a cozy Valentine’s Day dinner at a waterfront restaurant like Chart House or Carrol’s Creek Café.
Afterward, take a leisurely walk along the City Dock or Ego Alley. If you’re looking for a more private moment, plan a surprise sailboat ride. Many local companies offer private charters that can be tailored to your special occasion. Imagine popping the question as the sun sets over the bay, with the peaceful sound of waves in the background. It’s a moment that neither of you will ever forget.
St. Michaels also offers beautiful waterfront views and picturesque harbor. There are several high-quality hotels, inns, seafood restaurants, wineries, and locally owned gift shops. Say “I Do” overlooking the Chesapeake Bay.
2. A Rustic Barn Proposal

For a warm and intimate proposal, consider booking a visit to a barn wedding venue. Maryland is home to many beautiful barns, including Montagu Meadows in Carroll County. These rustic settings can be transformed into enchanting spaces with twinkling fairy lights, candles, flowers and amazing country views.
Plan a special Valentine’s Day picnic inside the barn or under the stars on the venue’s grounds. Arrange for a photographer to capture the moment when you pop the question. To make it extra personal, incorporate elements of your relationship into the setup. Perhaps photos of your favorite memories or your partner’s favorite flowers or candies. A barn proposal is not only romantic but also symbolic, as it hints at the next step: your wedding day.
3. A Romantic Mountain Overlook
If your partner loves the great outdoors, Maryland’s scenic overlooks provide a breathtaking backdrop for your proposal even in the winter. Popular spots like Sugarloaf Mountain, Catoctin Mountain Park, or the overlook at Cunningham Falls State Park offer sweeping views and serene settings.
Plan a day hike or a leisurely walk to the overlook and bring a picnic with you. Once you reach the perfect spot, surprise your partner with a heartfelt proposal with the mountains in the backdrop. For added romance, time it with the sunrise or sunset. If Valentine’s Day is chilly, pack a cozy blanket and a thermos of hot chocolate to keep warm while you celebrate your engagement.
4. A Winery or Brewery Proposal
Maryland is home to some fantastic wineries and breweries that can set the stage for an unforgettable proposal. Venues like Westminster Winery or Boordy Vineyards in Hydes offer scenic views, delicious drinks, and intimate atmospheres perfect for the occasion.
Plan a Valentine’s Day wine tasting or brewery tour, and coordinate with the staff ahead of time for a surprise. You could have the ring presented during a special toast or on a custom wine bottle labeled with “Will You Marry Me?” Many wineries and breweries have cozy seating areas by fireplaces, adding a warm and romantic vibe to your proposal.
5. A Surprise in Baltimore
For couples who love the city vibe, Baltimore has plenty of romantic spots to make your proposal unforgettable. Start the evening with a Valentine’s Day dinner at a fine dining restaurant like Charleston, The Capital Grille, or Tagliata.
After dinner, head to the Inner Harbor for a quiet moment by the water. You can also plan a proposal with a view by visiting Federal Hill Park or booking a private rooftop space overlooking the Baltimore skyline. For something truly unique, consider taking your partner on a Valentine’s Day helicopter tour of the city, ending with a proposal high above the glittering lights.

Making the Proposal Personal
No matter where you choose to pop the question, the key to a perfect proposal is making it personal. Think about what your partner loves most or think about your first date. Whether it’s nature, cozy settings, or lively cityscapes, tailor the experience to their preferences. Incorporate meaningful touches, like their favorite flowers, a playlist of your favorite songs, or a handwritten note expressing your love, excitement for the future and a beautiful ring.
If you want to capture the moment forever, consider hiring a photographer, content creator or videographer to document the proposal. Maryland has many talented professionals who specialize in engagement photography and can help you preserve this special day.
Valentine’s Day proposals are romantic, but Maryland’s diverse landscapes and venues make them even more magical. Whether you choose the scenic waterfront of Annapolis or St Michaels, the rustic charm of a barn venue like Montagu Meadows, located in Westminster, MD, the tranquility of a mountain overlook, the sophistication of a winery, or the vibrant energy of Baltimore, your proposal will be a day to remember.
Take the time to plan the details and create a moment that reflects your love story. After all, this is just the beginning of your next chapter together. With these ideas, you’re sure to sweep your partner off their feet and start your engagement on a truly unforgettable note. Remember Valentine’s Day is designed to celebrate love and what better way to do this is to get engaged.

Looking for a stunning barn venue? Montagu Meadows in Carroll County, MD, offers a breathtaking setting with a team dedicated to making your wedding day perfect. Reach out today to learn more about how we can bring your dream wedding to life!
Contact us today to start planning your dream wedding and discover how Mocha can transform your special day into a warm, timeless celebration!
Visit our Website: www.montagumeadows.com
Visit our gallery for additional photos: GALLERY | Montagu Meadows
Email us at: crkrone46@gmail.com
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Montagu Meadows is a locally owned and operated barn wedding venue located in Carroll County, Maryland. We are approximately 30 minutes south of Gettysburg, PA, 50 minutes west of Baltimore, and 1 hour from Washington, DC. We sincerely hope to encourage couples to learn more about the value and importance of choosing a locally owned business when it’s time to book your wedding venue and vendors. With locally owned venues you will often see a higher level of hospitality, better communication and a greater desire to truly ensure your wedding exceeds expectations. We are thrilled to support wedding venue owners from around the country with a weekly shout out in our blog. You can find locally owned wedding venues featured on this wedding venue map.
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