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Mid-Atlantic Coastal and Mountain Loop

A 6-day journey from New York City through the wild shores of Assateague, the scenic Blue Ridge Parkway, and the historic Shenandoah Valley, featuring key kosher dining hubs and iconic coastal crossings.

6days
17stops
1182km

The route

Tap a day or a town

You sleep in Cape May · Chincoteague · Charlottesville · Silver Spring · Baltimore — start and end in New York.

DAY01

Times Square → Cape May

307 km · 3h 21m driving · Overnight in Cape May Historic District
  1. 09:00
    Times Square· start
  2. 18 km · 28m
  3. 12:00
    West Side Kosher Meal Mart
  4. 289 km · 2h 53m
  5. 15:00
    ⭐ Cape May Historic District· overnight
DAY02

Cape May → Chincoteague

173 km · 3h 2m driving · Overnight in Chincoteague Island
  1. 09:00
    Cape May-Lewes Ferry· start
  2. 91 km · 1h 56m
  3. 12:00
    ⭐ Assateague Island National Seashore
  4. 82 km · 1h 6m
  5. 15:00
    Chincoteague Island· overnight
DAY03

Chesapeake Bay Bridge-Tunnel → Monticello

307 km · 3h 26m driving · Overnight in Monticello
  1. 09:00
    Chesapeake Bay Bridge-Tunnel· start
  2. 141 km · 1h 43m
  3. 12:00
    Richmond Kosher
  4. 166 km · 1h 43m
  5. 15:00
    ⭐ Monticello· overnight
DAY04

Big Meadows → Silver Spring

138 km · 2h 11m driving · Overnight in Silver Spring Kosher District
  1. 09:00
    ⭐ Big Meadows· start
  2. 88 km · 1h 21m
  3. 12:00
    Luray Caverns
  4. 50 km · 50m
  5. 15:00
    Silver Spring Kosher District· overnight
DAY05

National Aquarium → Baltimore

73 km · 1h 4m driving · Overnight in Baltimore Inner Harbor
  1. 09:00
    ⭐ National Aquarium· start
  2. 55 km · 40m
  3. 12:00
    Seven Mile Market
  4. 17 km · 24m
  5. 15:00
    Baltimore Inner Harbor· overnight
DAY06

Liberty Bell Center → Times Square

184 km · 2h 13m driving
  1. 09:00
    Liberty Bell Center· start
  2. 169 km · 1h 46m
  3. 12:00
    Shalom Pizza
  4. 15 km · 27m
  5. 15:00
    ⭐ Times Square
Booking timeline
Book these before you go
  1. Day 1Stay in Cape May · Night 1
  2. Day 2Stay in Chincoteague · Night 2
  3. Day 3Stay in Charlottesville · Night 3
  4. Days 4–5Stay in Silver Spring / Baltimore · Nights 4-5
Heads Up
  • Book the Cape May-Lewes Ferry in advance to ensure your vehicle slot.
  • Check Blue Ridge Parkway and Skyline Drive conditions for seasonal weather closures.
  • Verify kosher restaurant hours as many close early on Fridays or for holidays.