← The Weekend Getaways
🌿 RelaxedLong weekend · from Washington, DC

Sandy Shores, Gardens & Vineyard Wines

Escape the city for a sensory journey through Maryland's hidden gems, blending pristine beaches, botanical gardens, and award-winning vineyard tastings.

Day 1 — Sandy Point State ParkDay 2 — Cylburn ArboretumDay 3 — Catoctin Breeze Vineyard
Day 1Sandy Point State Park

Day 1Sandy Point State Park

🚗 1 hr 26 min driving📍 5 stops
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Morning
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Drive
Washington, DCSandy Point State Park
1 hr 3 min8:00 AM9:03 AM
Sandy Point State Park
Sandy Point State Park
4.4
Local beach & picnic area offering views of the Sandy Point Shoal Light & the Chesapeake Bay Bridge.
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Lunch
Libbey's Coastal Kitchen and Cocktails
Libbey's Coastal Kitchen and Cocktails
4.3
A Chincoteague, VA waterfront restaurant with a menu built around local clams, oysters, and blue crab. One of the best tables on Virginia's Eastern Shore, with the island's famous ponies as a backdrop.
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Afternoon
🚗
Drive
Sandy Point State ParkGreat Frogs Winery
14 min12:00 PM12:14 PM
Great Frogs Winery
Great Frogs Winery
4.5
Taste small-batch Maryland wines on a shaded terrace overlooking rolling vineyards. Relax with a flight of their signature blends while enjoying live music and local snacks.
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Evening
🚗
Drive
Great Frogs WineryCantler's Riverside Inn
9 min5:00 PM5:09 PM
Cantler's Riverside Inn
Cantler's Riverside Inn
4.5
Crack fresh steamed crabs while watching the sunset over the Chesapeake Bay at this legendary waterfront institution.
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Chesapeake Bay Beach Club
A resort and event property directly on the Chesapeake Bay in Stevensville, just across the Bay Bridge from Sandy Point State Park — the waterfront rooms face west across the bay toward Annapolis, and the sunset from the pier is one of the best views on the Chesapeake's western shore.
Day 2Cylburn Arboretum

Day 2Cylburn Arboretum

🚗 1 hr 49 min driving📍 5 stops
🌅
Morning
🚗
Drive
Sandy Point State ParkCylburn Arboretum
48 min8:00 AM8:48 AM
Cylburn Arboretum
Cylburn Arboretum
4.7
Tranquil park features 20+ gardens, century-old trees, a nature museum & a Civil War-era mansion.
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Lunch
R. House
R. House
4.5
A Baltimore food hall in a converted auto repair shop in the Remington neighborhood — chef-driven stalls in an energetic, high-ceilinged space. One of the city's best lunch destinations.
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Afternoon
🚗
Drive
Cylburn ArboretumBoordy Vineyards Inc
23 min12:00 PM12:23 PM
Boordy Vineyards Inc
Boordy Vineyards Inc
4.5
Sample award-winning estate wines in a historic stone winery, then stroll manicured grounds with panoramic views of Maryland's wine country. Pair tastings with local cheeses and charcuterie.
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Evening
🚗
Drive
Boordy Vineyards IncGuinness Open Gate Brewery
38 min5:00 PM5:38 PM
Guinness Open Gate Brewery
Guinness Open Gate Brewery
4.6
Tour the only Guinness brewery in the Western Hemisphere and sample perfectly poured pints in a vibrant taproom just outside Baltimore.
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The Ivy Hotel
A 1889 Victorian mansion in north Baltimore's Roland Park neighborhood, converted to Baltimore's most acclaimed boutique hotel — six suites in the original mansion and new rooms in the carriage house, with a Michelin-starred restaurant and a garden that borders the arboretum. A 5-minute walk from Cylburn.
Day 3Catoctin Breeze Vineyard

Day 3Catoctin Breeze Vineyard

🚗 2 hr 57 min driving📍 3 stops
🌅
Morning
🚗
Drive
Cylburn ArboretumCatoctin Breeze Vineyard
1 hr 19 min8:00 AM9:19 AM
Catoctin Breeze Vineyard
Catoctin Breeze Vineyard
4.5
Escape to this serene mountain vineyard nestled in the Catoctin Mountains where you can unwind with a glass of locally-produced wine while enjoying panoramic views and the gentle rustle of the breeze through the vines.
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Lunch
Rube's Crab Shack LLC
Rube's Crab Shack LLC
4.4
A laid-back Maryland crab shack near the Linganore wine trail — whole steamed blue crabs, crab cakes, and Old Bay by the fistful. The casual picnic-table setup is exactly what Chesapeake crab eating should feel like.
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Afternoon
🚗
Drive
Catoctin Breeze VineyardLinganore Winecellars
33 min12:00 PM12:33 PM
Linganore Winecellars
Linganore Winecellars
4.6
Sip Maryland and regional wines in a rustic barn setting surrounded by vineyard views. Browse their gift shop and settle onto the outdoor patio with a glass of their popular fruit wines.
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Evening
🚗
Drive
Linganore WinecellarsWashington, DC
1 hr 5 min5:00 PM6:05 PM
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