The Shepherdstown Cozy Crawl

 November 7–22, 2025

An Experience Shepherdstown initiative presented in partnership with Four Seasons Books

Shop Small. Stay Cozy. Win Big.
Kick off cozy season in Shepherdstown with a celebration of local flavor, community spirit, and small-town charm!
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The Shepherdstown Cozy Crawl runs November 7–22, encouraging shoppers to explore local favorites, collect stamps, and enjoy exclusive treats at participating businesses.

🎉 The official kickoff event will take place on Friday, November 7 at 5:00 PM with a book signing and launch event for Seasoned in Appalachia by Chef Jimmy Proffitt, hosted by Four Seasons Books in partnership with Alma Bea. This cozy evening of food, storytelling, and Appalachian heritage sets the perfect tone for two weeks of local celebration.

What Is the Cozy Crawl?
​Running from November 7–22, the Cozy Crawl transforms Shepherdstown into a celebration of comfort, connection, and community.
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Think of it as a mix between a self-guided holiday scavenger hunt and a cozy night in — only this time, you get to take the warmth with you.​

Start your journey by picking up a $5 Cozy Passport at any participating business.
Each passport includes:

• A beautifully designed booklet to collect stamps at each stop
• A free sample, small gift, or special offer from every participating business
• Access to exclusive discounts during the crawl
• Entry into the Grand Prize Drawing featuring a deluxe Shepherdstown gift basket
• And a built-in excuse to sip cider, shop local, and slow down

Proceeds from passport sales help support Shepherdstown community events all year long.

The Shepherdstown Cozy Crawl Basket Giveaway
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Complete five or more stops, return your passport, and you’ll be entered to win the Downtown Cozy Basket — a deluxe prize filled with books, food, handmade goods, and local gifts from all participating businesses.
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The drawing will take place Sunday, November 23 at the Shepherdstown Farmers Market.

How It Works

1. Purchase your $5 Cozy Passport:
   • Available now for online purchase at www.fourseasonsbooks.com with pickup at Four Seasons Books, or
   • In-store at Four Seasons Books beginning November 7.
2. Visit participating shops between November 7–22 to collect stamps.
3. Fill in your name, email, and phone number inside your passport.
4. Return your completed passport to Four Seasons Books by November 22 to enter the Downtown Cozy Basket Giveaway.
5. The Grand Prize Drawing will be held on Sunday, November 23 at the Shepherdstown Farmers Market.

What’s Included
Your $5 passport includes:

• A collectible booklet to track your cozy crawl adventure
• Complimentary samples, discounts, or surprises at each stop
• Access to crawl-only in-store specials and events
• Automatic entry into the Downtown Cozy Basket Giveaway (valued at $250+)

Participating Businesses

• Four Seasons Books
• Alma Bea
• Mountaineer Popcorn Company
• Shepherdstown Pedal & Paddle
• Tonic Herb Shop & Elixir Bar
• Dogwood General Store
• Admiral Analog’s
• Wind Gap Music
• Game Knights
• German Street Marketplace
• Grapes & Grains Gourmet
• Reversa Rose Skincare
• Sand & Pine
• Nightburner Print Company

Why Join? The Cozy Crawl is part of the Experience Shepherdstown initiative — a collaborative effort to celebrate and uplift the small businesses that make our downtown special.
When you shop local, you help keep Shepherdstown’s creative, welcoming spirit alive.

Presented By Four Seasons Books & Experience Shepherdstown, proudly supporting local business, creativity, and community since 1991.

Cozy Crawl Passport

$5.35

Your Ticket to Cozy Season in Shepherdstown

Get ready to sip, shop, and stroll your way through downtown during the Downtown Shop Crawl: The Cozy Crawl, happening November 7–22, 2025.

Your Cozy Passport is your all-access pass to special discounts, treats, and local charm at every stop.

Each passport includes:

• A beautifully designed booklet to collect stamps at each participating business
• Access to Crawl-only discounts throughout downtown
• Automatic entry into the Downtown Cozy Basket Giveaway — a grand prize filled with books, handmade goods, gift cards, and local treats
• The satisfaction of supporting small businesses that make Shepherdstown shine

How It Works

1. Purchase your Cozy Passport online or at any participating shop.
2. Visit downtown businesses between November 7–22 to collect stamps.
3. Earn a stamp at each stop by showing your passport and enjoying your exclusive offer or sample.
4. Complete at least five stops to qualify for the Grand Prize Drawing.
5. Submit your completed passport by November 22 — the winner will be announced at the Farmers Market on November 23.

Why You’ll Love It

The Cozy Crawl isn’t just shopping — it’s community. It’s warm drinks, friendly faces, and the magic of a small-town holiday season, all while supporting the independent businesses that make Shepherdstown special.

Join us in making downtown the coziest place to be this November.

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