Southern Maryland is like the best-kept secret of the DMV—close enough for out-of-town guests to get here without a travel saga, but just far enough to feel like an actual escape.

Spend a weekend in the quiet southwest corner of the state and explore the earliest beginnings of Maryland from the first colony on St. Clement’s Island to the site of its first capital, St. Mary’s City. Along with fascinating history, you’ll discover friendly folks, serene landscapes and fresh bay-to-table dining.

– Ellen Honey of Marina Life

You’re surrounded by vibrant small towns like…

• La Plata – Home to The Charles, boutique shopping, and sweet Southern charm

• Leonardtown – A historic arts district with wine tastings, galleries, and riverside dining

• Solomons Island – A coastal town perfect for crab feasts, boardwalk strolls, and boat rentals

• St. Mary’s City – Maryland’s first colonial capital, filled with walking trails and timeless views

Here, your guests won’t be stuck Googling “things to do near my hotel.” They’ll be sipping local wine, kayaking through a ship graveyard, or taking golden hour selfies on the pier before the main event even starts.

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Wedding Weekend Goals, Southern Maryland Style

🍷 Winery crawls framed by waterfront, not parking lots

🚤 Private charter cruises on the Potomac

🦀 Group crab feasts with waterfront sunsets

🛍️ Local boutiques, art walks, and antique treasure hunts

🍳 Cozy brunch spots and coffee shop meetups the morning after

It’s the kind of wedding weekend that feels less like an obligation—and more like a mini vacation everyone actually wants to attend.

Wedding weekends shouldn’t start with stress and end with a spreadsheet. The lead-up to your “I do” should feel like a celebration, not a scavenger hunt of meetings and errands. Whether you’re arriving a few days early or just want to make the most of your planning experience before the festivities kick off, here’s how to keep the momentum going without burning out.

✨ Planning Time That Feels Like Us-Time

Before the chaos of boutonnières and bustle loops, take a beat to enjoy your surroundings—and each other. Southern Maryland offers plenty of ways to slow down and soak in the calm before the celebration.

• Treat yourselves to a spa day at Hands of Gold Spa in La Plata or Massage Therapy of Fredericksburg, just across the Potomac

• Sip and savor your way through a casual winery crawl at Port of Leonardtown, Xella Winery, or Running Hare Vineyard

• Book a sunset cruise or check out the ghost fleet at Mallows Bay, then grab dinner at The Charles or dockside at The Pier in Solomons

• Unplug with a walk through Jefferson Patterson Park or an afternoon at Historic St. Mary’s City—it’s history with a breeze

All these activities could also be reserved for guest activities or your mini-moon if you’re staying local after saying “I Do” at The Pavilion.

📋 Vendor Meetings Made Easy

Meeting with local vendors doesn’t have to be a headache. Map out a loose itinerary if you have a day to spare, so you’re not sprinting from salon to signage shop. Keep it light, give yourself buffer time, and balance every task with a treat.

Sample Itinerary:

• Morning coffee + pastries at Botanic Cafe

• Floral mock-up at your florist’s studio

• Caterer tasting mid-morning

• Final venue walkthrough at Weatherly with your planner (hi, it’s us)

• Hair and makeup trial mid-afternoon

• End with cocktails and crabcakes at The Front Porch or Brudergarten

Want to keep things extra streamlined? Group your meetings by location and coordinate a few vendors to meet you on-site at Weatherly. One drive, several checkmarks, zero stress.

🚐 Transportation Tips

We’re not saying you need a party bus… but we’re also not not saying it. Here’s how to keep everything moving smoothly…

• Charter a shuttle or sprinter van for rehearsal night + wedding day (local companies like Keller Transporation are great)

• Send a shared Google Map with key locations—lodging, ceremony, dinner, brunch

• Coordinate carpools among your wedding party for vendor runs and errands

The Pavilion at Weatherly gives you the kind of space that instantly sets the tone: elegant, welcoming, and deeply rooted in natural beauty. With 600 feet of private Potomac River shoreline and beach access, a glass-walled pavilion with panoramic views, and a historic manor house for pre-ceremony prep, we’ve curated a setting that’s breathtaking without being overdone.

What makes it so special? For starters, there are no double bookings. No crowds. No strangers strolling past your ceremony. It’s just you, your people, and a private estate that feels like your own slice of Southern Maryland.

We’re designed for full weekend flow. From hosting your rehearsal dinner in the pavilion to splash golf into the Potomac and golden hour portraits by the pier, every part of your wedding weekend can orbit around one stunning space. And while we don’t offer on-site lodging, we’re surrounded by charming inns, hotels, and waterfront Airbnbs your guests will love.

Want a vendor to meet you on-site? No problem. Want to create a seamless experience that keeps your guests grounded and relaxed all weekend long? That’s our specialty.