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3 days
Canada, North America

3-Day Winchester itinerary guide

Use this route structure as a starting point, then adapt stops and timing with your group in Journii.

Winchester — Winchester Hotel

Top stops to prioritize

  • Apple Blossom Mall
  • Cork Street Tavern
  • Bonnie Blue Southern Market & Bakery
  • Brewbakers Restaurant
  • Museum of the Shenandoah Valley
  • 50/50 Taphouse
  • Jim Barnett Park
  • Hopscotch Coffee & Records

Day 1: Most popular attractions

For day 1, we strategically grouped the most popular attraction, Museum of the Shenandoah Valley, with surrounding point of interests to start your trip off with a bang.

  • Apple Blossom Mall
  • Jim Barnett Park
  • Hopscotch Coffee & Records
  • Old Town Winchester

Day 2: Center of town

For day 2, we recommend exploring the center side of town.

  • Bonnie Blue Southern Market & Bakery
  • Bright Box Theater
  • Roma Old Town Wood-Fired Pizzeria
  • Union Jack Pub & Restaurant
  • Village Square Restaurant
  • Red Fox Creamery

Day 3: Proximity is everything

For day 3, we bundled attractions like Museum of the Shenandoah Valley and Shenandoah Valley Discovery Museum and other places within a close range, so that the time it takes to travel between all of them is less than...

  • Museum of the Shenandoah Valley
  • Shenandoah Valley Discovery Museum
  • Shenandoah Valley Civil War Museum
  • Winchester Brew Works
  • Violino Ristorante Italiano

Related itinerary guides

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