Cutest Towns in Maryland for a Wedding in 2026
If you’re dreaming of a charming, picturesque, and unforgettable place to say “I do,” Maryland is filled with beautiful small towns that feel straight out of a storybook. From waterfront villages to historic cobblestone streets, the state offers endless wedding-worthy backdrops perfect for couples planning a Maryland wedding in 2026.
Here are the cutest towns in Maryland for a wedding, each with its own distinct charm, scenery, and romantic feel.
1. St. Michaels — The Quintessential Waterfront Romance
When people picture a Maryland wedding, St. Michaels often comes to mind. This Chesapeake Bay treasure offers sailboats, sunsets, and boutique inns—ideal for couples who want an upscale coastal vibe.
Why it’s perfect:
Stunning waterfront venues and marinas
Quaint streets filled with local shops and seafood restaurants
Ideal for weekend-long wedding celebrations
Best for: Waterfront weddings, intimate celebrations, and luxury coastal events.
2. Chestertown — Colonial Charm Meets River Views
Located along the Chester River, Chestertown is known for its colonial architecture and artistic atmosphere. It’s an excellent choice for couples who want history, charm, and a scenic, walkable downtown.
Why couples love it:
Brick sidewalks, historic homes, and gorgeous gardens
Riverfront parks and timeless churches
Beautiful fall foliage for autumn weddings
Best for: Historic venues, vintage aesthetic, and classic Eastern Shore weddings.
3. Ellicott City — Cobblestones, Character, and Cozy Vibes
Old Ellicott City feels like a romantic movie set with its stone buildings, winding streets, and eclectic shops. It’s perfect for couples wanting a charming town with both rustic and elegant venue options.
What stands out:
Unique venues nestled in historic mills
Amazing photography backdrops (stone architecture, bridges, streams)
A lively Main Street full of personality
Best for: Rustic-chic weddings, charming winter weddings, and couples who love character.
4. Annapolis — Nautical Elegance and Timeless Beauty
Maryland’s capital may be small, but it’s packed with charm. With its historic district, waterfront docks, and iconic architecture, Annapolis is a dream wedding destination.
Why it’s a top pick:
Naval Academy, waterfront piers, and 18th-century streets
Seasonal boat parades and Chesapeake sunsets
Tons of hotels for out-of-town guests
Best for: Classic, nautical, and formal weddings.
5. Havre de Grace — A Sweet Waterfront Town with Lighthouse Views
Set at the top of the Chesapeake Bay, Havre de Grace offers calm waters, boardwalk strolls, and the iconic Concord Point Lighthouse—a picture-perfect wedding photo spot.
Why it’s adorable:
Scenic waterfront promenade
Small-town feel with modern touches
Beautiful parks and nature views for outdoor ceremonies
Best for: Outdoor, waterfront, or garden-style weddings.
6. Berlin — One of America’s Coolest Small Towns
Named one of the “Coolest Small Towns in America,” Berlin is overflowing with charm. Its tree-lined streets and Victorian architecture make it an incredible choice for weddings with a whimsical, vintage, or boho feel.
Why couples love Berlin:
Cute downtown full of boutiques and cafés
Horse-drawn carriages and historic buildings
Close to Ocean City for honeymoon fun
Best for: Vintage, bohemian, and small-town-romantic weddings.
7. Frederick — Historic Streets and Mountain Views
Frederick blends charming historic streets with gorgeous rolling landscapes just outside town. It’s an amazing destination if you want variety: downtown elegance, countryside barns, vineyards—Frederick has it all.
Highlights:
Beautiful creek walk area for photos
Dozens of wineries and farms nearby
A lively downtown with great dining for rehearsal dinners
Best for: Vineyard weddings, barn weddings, and hybrid city-country celebrations.
Final Thoughts: Where Will You Say “I Do” in 2026?
Maryland’s small towns offer something for every couple—coastal romance, historic charm, rustic backdrops, and vibrant downtowns. Choosing one of these cute Maryland towns for your 2026 wedding ensures a celebration that feels personal, picturesque, and unforgettable.
