🌿 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 1 — Sandy Point State Park
Day 1 — Sandy Point State Park
🚗 1 hr 26 min driving📍 5 stops
🌅
Morning
🚗
Drive
Washington, DC → Sandy Point State Park
1 hr 3 min8:00 AM → 9:03 AM
Sandy Point State Park
★ 4.4Local beach & picnic area offering views of the Sandy Point Shoal Light & the Chesapeake Bay Bridge.
9:03 AM📍 See location
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Lunch
Libbey's Coastal Kitchen and Cocktails
★ 4.3A 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.
10:03 AM📍 See location
☀️
Afternoon
🚗
Drive
Sandy Point State Park → Great Frogs Winery
14 min12:00 PM → 12:14 PM
Great Frogs Winery
★ 4.5Taste 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.
12:14 PM📍 See location
🌙
Evening
🚗
Drive
Great Frogs Winery → Cantler's Riverside Inn
9 min5:00 PM → 5:09 PM
Cantler's Riverside Inn
★ 4.5Crack fresh steamed crabs while watching the sunset over the Chesapeake Bay at this legendary waterfront institution.
5:09 PM📍 See location
🛏️
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 2 — Cylburn Arboretum
Day 2 — Cylburn Arboretum
🚗 1 hr 49 min driving📍 5 stops
🌅
Morning
🚗
Drive
Sandy Point State Park → Cylburn Arboretum
48 min8:00 AM → 8:48 AM
Cylburn Arboretum
★ 4.7Tranquil park features 20+ gardens, century-old trees, a nature museum & a Civil War-era mansion.
8:48 AM📍 See location
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Lunch
R. House
★ 4.5A 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.
9:48 AM📍 See location
☀️
Afternoon
🚗
Drive
Cylburn Arboretum → Boordy Vineyards Inc
23 min12:00 PM → 12:23 PM
Boordy Vineyards Inc
★ 4.5Sample 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.
12:23 PM📍 See location
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Evening
🚗
Drive
Boordy Vineyards Inc → Guinness Open Gate Brewery
38 min5:00 PM → 5:38 PM
Guinness Open Gate Brewery
★ 4.6Tour the only Guinness brewery in the Western Hemisphere and sample perfectly poured pints in a vibrant taproom just outside Baltimore.
5:38 PM📍 See location
🛏️
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 3 — Catoctin Breeze Vineyard
Day 3 — Catoctin Breeze Vineyard
🚗 2 hr 57 min driving📍 3 stops
🌅
Morning
🚗
Drive
Cylburn Arboretum → Catoctin Breeze Vineyard
1 hr 19 min8:00 AM → 9:19 AM
Catoctin Breeze Vineyard
★ 4.5Escape 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.
9:19 AM📍 See location
🍽️
Lunch
Rube's Crab Shack LLC
★ 4.4A 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.
10:19 AM📍 See location
☀️
Afternoon
🚗
Drive
Catoctin Breeze Vineyard → Linganore Winecellars
33 min12:00 PM → 12:33 PM
Linganore Winecellars
★ 4.6Sip 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.
12:33 PM📍 See location
🌙
Evening
🚗
Drive
Linganore Winecellars → Washington, DC
1 hr 5 min5:00 PM → 6:05 PM
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