Pirates & Wenches Weekend 2026: Celebrating Rock Hall’s Waterfront Spirit

Rock Hall came alive with pirate spirit during the 19th annual Pirates & Wenches Fantasy Weekend, held August 7–9, 2026. This popular family-friendly tradition brought residents and visitors together for a lively weekend filled with costumes, music, local food and waterfront fun. Throughout the weekend, Main Street was transformed into a colorful pirate village. Performers, local vendors and visitors dressed in creative costumes filled the town with energy and entertainment. Children also enjoyed games, a treasure dig and other activities created especially for young pirates.


The celebration continued along Rock Hall’s waterfront with harbor festivities, a decorated…

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August is a wonderful time to experience Maryland’s Eastern Shore.

From waterfront festivals and live music to historic downtowns and Chesapeake Bay traditions, there are plenty of ways to enjoy the final weeks of summer.

Here are a few local events and activities to add to your August calendar.

First Friday in Chestertown

Spend the evening exploring downtown Chestertown’s locally owned shops, galleries and restaurants. First Friday is a great opportunity to enjoy the town’s historic charm and walk along the Chester River.

Pirates & Wenches Weekend in Rock Hall

Rock Hall celebrates one of its most popular summer traditions with pirate-themed entertainment, costumes, music and family activities.

While you are there, visit the…

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 A Boater’s Paradise at 110 Channel Marker Way #203

For buyers seeking a luxury waterfront home with boating access and minimal exterior maintenance, 110 Channel Marker Way #203 in Grasonville offers a remarkable Eastern Shore lifestyle.

Located in the Wells Cove community, this four-bedroom, four-bathroom residence provides approximately 2,653 square feet of living space across three levels. A private elevator makes every floor easily accessible.

The main level is warm and inviting, with an open kitchen, fireplace, and guest bedroom with an en-suite bathroom. That bedroom is currently used as an office, demonstrating the floor plan’s flexibility.

Upstairs, the primary suite opens to a private balcony overlooking the water. Two additional…

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Country Elegance in the Clearview Community at 24274 Waterview Drive

For buyers who want space, privacy, and access to the water without maintaining a private waterfront estate, 24274 Waterview Drive in Worton offers a compelling alternative.

This updated Cape Cod is located in the water-oriented community of Clearview, only minutes from Historic Chestertown. The neighborhood includes Franklin Pond, open community space, and access to Churn Creek.

The four-bedroom residence offers approximately 3,006 square feet of finished living space on 4.39 acres. Over the last two years, the home has undergone a significant transformation that includes updates to the kitchen, bathrooms, flooring, landscaping, and HVAC system.

The main-level primary…

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Waterfront Recreation and Privacy at 24050 Macs Lane 

 24050 Macs Lane in Worton is much more than a home near the water. It is a 5.48-acre waterfront retreat designed around the outdoor experiences that make Maryland’s Eastern Shore so special.

The property sits along Churn Creek and includes a private dock with boating access to the Chesapeake Bay. Owners can fish, crab, sail, waterski, kayak, and explore the region’s waterways directly from home.

Closer to the shoreline, a board-and-batten cabin creates a convenient base camp for water sports and afternoons by the creek. The grounds also include a barn with a stall suitable for a horse or sheep, a detached two-car garage with a lounge above it, and a nature trail for walking through the…

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The Tilley Residence: Historic Architecture Reimagined at 105 High Street

Some homes occupy an address. Others become part of a town’s identity. 105 High Street in Chestertown belongs firmly in the second category.

Known as the Tilley Residence, this five-bedroom home was rebuilt in 1863 and is an exceptional example of Second Empire architecture. Its prominent position near the foot of High Street places it across from the historic Custom House and only one block from the Chester River waterfront.

The residence underwent an extensive restoration completed in 2025. The work respects the home’s architectural character while introducing updated systems, refined finishes, and the comforts expected in a modern luxury property.

Inside,…

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Country Living and Flexible Income Potential at 12712 and 12714 Still Pond Road

If you are searching for a versatile property near Chestertown, Maryland, 12712 and 12714 Still Pond Road deserves a closer look. This six-bedroom duplex offers approximately 4,305 square feet of space and several compelling ways to use it.

An owner could live in one side while renting the other, lease both residences as an investment, or create a comfortable multigenerational home. That flexibility is what makes the property particularly interesting. It provides room for changing family needs while also presenting an opportunity to generate income.

The oversized garage adds even more usable space. It includes a kitchenette, full bathroom, and loft that could…

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Another strong result here on the Eastern Shore.

204 Rolling Road in Chestertown just closed — and it’s a perfect example of what happens when preparation, pricing, and positioning all align.

This property hit the market with a clear strategy from day one. We focused on highlighting the home’s livability, setting, and overall value within the Chestertown market. By combining targeted digital exposure with strong presentation, we were able to generate immediate interest.

The result?
A quick sale and a great price.

That’s not luck — that’s execution. In today’s market, buyers move fast when they recognize value. The key is making sure they see it clearly the moment your home hits the market. That comes down to:

-Strategic pricing

…

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201 Birch Run Road in Chestertown offers a compelling blend of updates, outdoor living, and walkable lifestyle—all set on a quiet cul-de-sac with views of the Chester River and close proximity to Washington College, shops, restaurants, and parks.

Thoughtful Updates

This home has been improved where it counts. In 2021, updates included joist work, flooring, crawl space encapsulation, and rear fencing, creating a strong foundation for long-term ownership. In 2025, the rough cut cedar siding was freshly repainted, enhancing both durability and curb appeal.

Indoor-Outdoor Living

The property is designed to be enjoyed. A private courtyard with a water feature offers a quiet retreat, while the spacious, partially shaded backyard with deck and…

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A Rare Development Opportunity on Maryland’s Eastern Shore

Opportunities like this are becoming increasingly rare in today’s market.

Located just minutes from Downtown Chestertown, 0 Round Top Road offers 5.81 acres of cleared, level land positioned along a key commercial corridor. With Suburban Commercial (SC) zoning, this property presents a unique chance for investors, developers, and business owners to secure land in one of the Eastern Shore’s most desirable and steadily growing areas.

Strategic Location with Real Potential

Location is everything in real estate. This property delivers.

Round Top Road sits in a highly accessible area just outside the historic core of Chestertown. It offers excellent visibility and convenience while…

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