25 Best Places to Propose in Maryland

December 18, 2023 – Posted in: Jewelry Blog

Are you ready to propose to the love of your life in Maryland? If so, we’ve curated a selection of unique proposal locations to help you find the best spot. From waterfronts and Islands to gardens and museums, Maryland has breathtaking landscapes and romantic settings to create a lasting proposal memory.

1. Take a Carriage Ride Along the Brandywine, MD Wine Tail

Brandywine MD Wine Tail big green land during sunset

Picture you and your soon-to-be spouse taking a romantic carriage ride while sipping wine and enjoying views of the pretty farmland vistas. Enjoy nature along the Legacy Wine Trail as you learn about this rare historic farming community. Brandywine Carriage Tours will treat you to a wine tasting at Janemark Winery and Vineyard, and their package includes the ride, wine, and snacks.

2. The King and Queen Seat Overlook

king and queen seat overlook rocks and trees

This spectacular scenic overlook is one of the most popular places in Maryland and great for outdoor enthusiasts who love rock climbing and hiking. The overlook has a beautiful spot to propose: the King and Queen Seat. The loop continues through a forest and crosses some streams along the White and Blue Trails. The Rocks Chrome Hill Road is where the trail begins and ends.

3. Downtown Annapolis

small town decorated for holidays of Annapolis

You and your partner can shop, dine, enjoy music, history, and much more in the beautiful Downtown Annapolis. Sit on the seawall, watch the sailboat races, and see why Annapolis is “America’s Sailing Capital.” Enjoy a romantic stroll along the lovely waterfront with its beautiful scenery and experience the City Dock charm, making for a memorable proposal moment.

4. The National Aquarium

National Aquarium with fish plants

If your partner loves dolphins, this proposal location will blow her away! Picture you and your partner petting a dolphin, watching it do tricks, and then dropping to one knee to pop the question. Aside from getting close to the dolphins, several award-winning exhibits feature unique aquatic habitats and 4D movie experiences.

5. The Wisp Ski Resort

wisp ski resort  snow proposal location

For a weekend of fun and adventure and several opportune moments to get down on one knee to propose, the Wisp Ski Resort has it all!

Here are some of the adventurous activities for you and your boo:

  • Whitewater rafting and kayaking
  • Mountain adventures
  • Ariel adventures
  • Golf
  • Lake adventures
  • Escape games
  • Tubing

You could also fill your car tank, courtesy of the resort, and take a scenic ride to the beautiful mountains of Maryland, passing lovely painted trees in Garrett County.

6. A Hot Air Balloon Ride

hot air balloon on top of the mountains during sunset

If you’re happy to splurge, a surprise hot air balloon ride proposal will be an extravagant, mesmerizing experience. It’s romantic, adventurous, and unique. Take in the spectacular views while you and your partner drift off into the sunset as the crew from Sky Candy Ballooning roll out a banner asking that important question, “Will you marry me?” After the flight, you’ll be given a special memento to celebrate your engagement.

7. Quiet Waters Park in Annapolis

water and rocks next to a bridge during sunset

This breathtaking park is an oasis of tranquility and perfect for an intimate proposal. There’s a mesmerizing waterfront, and you and your true love can take a romantic stroll along the paved trails. You could also propose on the bridge. As the sun sets, it casts an enchanting glow on the calm waters, providing a perfect proposal moment. If your partner loves art, there are art galleries that exhibit amazing local and regional pieces. Better still, you can rent an outdoor pavilion for an engagement party!

8. Chesapeake Bay Maritime Museum

picture of the chesapeake bay maritime museum

In St. Michaels, the Chesapeake Bay Maritime Museum is a magical proposal location. You and your partner can navigate the perfectly restored exhibits, the charming lighthouse, and historic boats. Then, as the day ends, you can get down on one knee and propose on the pretty waterfront.

9. Historic Annapolis

houses and trees in the historic Annapolis

Stroll through the romantic Historic Annapolis’s cobblestoned streets hand in hand with your boo. Pop into the iconic Maryland Statehouse, the nation’s oldest, then move on to the glorious City Dock and watch the boats sail gently by. The perfect moment to propose!

10. Sherwood Gardens

garden with flowers, grass and trees Sherwood Gardens

If you regularly spoil your betrothed with flowers, go the extra mile and propose amongst thousands of gorgeous blooms. Sherwood Gardens has been around since 1920 and impresses all year round with beautiful magnolias, azaleas, and tulips. With more than six acres of flowery delights, you’ll have several opportunities to ask your special person to marry you. The ideal time to visit the gardens is the end of April into the start of May. There’s no need for a reservation, and entry is free.

11. Catoctin Mountain Park

picture of the catoctin mountain pier with mountains and rocks

For outdoorsy couples, Catoctin Mountain Park is the perfect proposal getaway. You and your love can hike up to one of the gorgeous outlooks like Thurmont Vista or Hog Rock and feast your eyes on the panoramic views of dense forests and rolling hills. The perfect proposal backdrop. There are picnic areas and hiking trails, and you can camp or rent one of the historic cabins for a romantic evening under the stars.

12. Boordy Vineyards

vineyard in front of the mountains during a sunny day

If you and your partner enjoy wine tasting, Boordy Vineyards in Baltimore County is a fabulous proposal location with stunning surroundings. It’s Maryland’s oldest family-run winery, and only a 15-minute ride north of the Baltimore Beltway. The farm is a 19th-century charm, boasting rows of vines, interesting buildings, and shady picnic spots. Perfect for proposing to the love of your life.

13. Ladew Topiary Gardens

picture of the ladew topiary gardens

These fantastic gardens are one of the ten best topiary gardens in the world. A magical wonderland of stunning flowers and sculpted greenery, you can walk with your partner amongst the award-winning beauty of the gardens until you find the right spot to propose.

14. Patapsco Valley State Park

picture of the patapsco valley state park with water and trees around

You won’t run out of picturesque proposal spots in this beautiful park with cascading waterfalls and divine riverside overlooks. Here are some fun activities to do with your betrothed:

  • Camping
  • Hiking
  • Fishing
  • Canoeing
  • Mountain bike trails
  • Horseback riding
  • Picnicking

15. Maryland State House

picture of the maryland state house

In downtown Annapolis, this magnificent historical building resides within State Circle. It’s the oldest state capitol still in legislative use and the only state house ever serving as the nation’s capitol. Picture yourself dropping to one knee during a self-guided tour of this majestic structure. Alternatively, if you’d prefer something more intimate, propose in the relaxing gardens at the front of the building. The impressive architecture and gorgeous surroundings provide a lovely proposal setting.

16. Charleston Restaurant in Baltimore

charleston restaurant in baltimore with table set outside

This proposal option is for the foodies. Make your loved one feel like royalty and treat them to a delicious feast in the Charleston restaurant. This five-star Diamond-rated restaurant has won several awards, including the Best Wine List and received four stars on Forbes. It’s incredibly romantic, and the New York Times called their food splendid! They offer a combination of country favorites and French food for a delicious, unique culinary experience with a divine atmosphere to pop the question.

17. William Paca House & Garden

picture of green land and mountains with water at the william paca house and garden

What could be more romantic than a stunning 18th-century Georgian mansion? Located in the historic district of Annapolis, the mansion once housed William Paca, who signed the Declaration of Independence. Propose while touring the mansion and learning about its history or strolling through the breathtaking walled garden. The mansion’s romantic ambiance creates the ideal location for a memorable proposal.

18. Carroll Creek Park in Frederick, MD

picture of carroll creek park in frederick

This downtown park has several pedestrian bridges with colorful murals, majestic trees, and gorgeous floral blooms during spring. Shops, gardens, and restaurants flank it, and its beautiful setting provides many wonderful spots to propose, whether with an audience or in private.

19. Brookside Gardens

garden surrounded by flowers and trees

Brookside Gardens is an award-winning 50-acre public garden in Wheaton Regional Park. The different gardens include:

  • Azalea Garden
  • Aquatic Garden
  • Butterfly Garden
  • Rose Garden
  • Children’s Garden
  • Trial Garden
  • Japanese Style Garden
  • Woodland Walk
  • Rain Garden

The formal gardens have the Maple Terrace, Yew Garden, Perennial Garden, and Fragrance Garden. Proposal spots can be near shimmering ponds, green lawns, colorful gardens, and romantic gazebos. And to celebrate your special day, you can party with family and friends in the conservatory or contemporary reception hall, which are available all year round. Admission to the gardens is free.

20. Assateague Island

picture of assateague island with horses and sea

Assateague Island is a beautiful gem for nature enthusiasts. Its pristine beaches feature plenty of wild horses and various birds. With 37 miles of gorgeous beaches, it has fantastic activities you and your partner can enjoy:

  • Wildlife photography
  • Ranger-guided programs
  • Hiking on nature trails
  • Biking
  • Horseback riding
  • Crabbing
  • Fishing
  • Swimming and surfing
  • Kayaking and canoeing

You and your partner can also try primitive camping on the ocean and Assateague Island. There are seafood restaurants, and if camping isn’t your thing, stay at a cottage, hotel, bed and breakfast, or beach house. This Island has many adventurous and romantic spots where you can ask your partner to marry you.

21. Great Falls Park

falls park with waterfalls and rocks all around with trees

Found along the Potomac River, this mesmerizing park gives you gorgeous views of dramatic cliffs and cascading waterfalls. There are many glorious hiking trails, but choose the Billy Goat Trail for a spectacular up-close experience. For historical exhibits and interpretive programs, pop by the Great Falls Tavern built in 1828. And for a unique experience, take a mule-drawn canal boat ride from this amazing location.

22. Smith Island

smith island with picture of the blue sea

Fancy a trip to a remote island with breathtaking scenery and delicious homemade Smith Island cakes? In the Chesapeake Bay, Smith Island is so isolated that its residents speak with a relic accent even today. It’s one of the oldest English-speaking settlements in the region and is only accessible by boat. The island can easily be explored on foot, canoe, kayak, or bicycle. If you want to spend a night on the island, you can book a guest cottage or local bed and breakfast and indulge in the tasty seafood meals. There are various gift shops to purchase souvenirs. Plus, you and your love can participate in wildlife watching, birdwatching, crabbing, and fishing. Book an artifact tour to visit the pretty Island waterways.

23. Linganore Winecellars

lineganore winecellars in a cave

Another fantastic vineyard proposal location is Linganore Winecellers. This 230-acre estate is surrounded by rolling vineyards, breathtaking vistas, and a delightful lake. It has a cozy tasting room and many beautiful spots for a magical proposal. This secluded vineyard is in Frederick and open all year round. They have amazing staff to assist you with creating your memorable proposal moment.

24. The Annapolis Waterfront Hotel

picture of the annapolis waterfront hotel with lights and boardwalk

Treat your partner to a day or weekend away at the Annapolis Waterfront Hotel. Aside from the romantic waterfront, you and your partner can marvel at the untouched colonial architecture and calming Chesapeake Bay vistas. This fantastic hotel provides an intimate getaway experience in the heart of Maryland’s capital. They offer a “Love on the Harbor” Package which includes:

  • A bottle of sparkling wine in your room upon arrival
  • Overnight stay
  • Breakfast at Pusser’s Caribbean Grille

25. The Baltimore Waterfront Promenade

image of the baltimore waterfront promenade in front of buildings

Another waterfront option is the Baltimore Waterfront Promenade. It’s eight miles long and great for walking or biking. You and your love can enjoy the views of the Patapsco River harbor and entertain yourselves with the various stores, public spaces, and dining areas. The Inner Harbor has many attractions and museums, including the National Aquarium, which is popular with Maryland tourists. Check out the USS Constellation, the only surviving, intact naval vessel from the Civil War. Other interesting places along the promenade include the Port Discovery Children’s Museum and the Maryland Science Center. Along the waterfront, there are many attractive spots for engagement photos.

Talk to a Diamond Expert

talk to afshin or benjamin to buy anything from the showroom

By now, you’ve probably chosen the proposal location. All that’s left to do is buy the ring! It would be best to have a ring that will dazzle your partner, and Estate Diamond Jewelry isn’t short of dazzling ring choices. We have unique antique and vintage rings, and we can assist you in finding one that suits your partner and your pocket.

Contact us for questions and to view our unique pieces.