A sweet downtown holiday tradition

The Great Middletown Cookie Crawl 2026Middletown, Delaware

One box, a downtown stroll, and a different holiday cookie at every stop.

Pick up your official cookie box on Cochran Square after the Holiday Spectacular Parade, then stroll downtown to 13 participating downtown merchants. Each stop adds one unique holiday cookie to your box.

Saturday, December 5, 2026 · Downtown Middletown

Preorder your cookie box

$20 per cookie box when you preorder online (up to two per order). A limited number of cookie boxes will be available to purchase onsite for $30.

How it works

Fill your box, one stop at a time

The Cookie Crawl follows the parade, so you can make a whole holiday morning of it downtown.

Preorder your box

Preorder online for $20 per cookie box, up to two boxes per order. Online preorders are limited, so get yours ahead of time.

Check in after the parade

Check in at our table on Cochran Square (corner of Broad and Main Streets) to get your cookie box and your list of stops.

Collect your cookies

Visit 13 participating downtown merchants for one cookie at each stop, all baked by Sweet Melissa's. By the end, your box is full of different holiday cookies.

Plan ahead

Cookie Crawl details

Date: Saturday, December 5, 2026
Start time: 11:00 AM–2:00 PM, right after the Holiday Spectacular Parade
Location: Downtown Middletown, Delaware
Check-in: Check in at our table on Cochran Square (corner of Broad and Main Streets) to get your cookie box and your list of stops.
Stops: 13 participating downtown merchants
Price: $20 per cookie box when you preorder online. A limited number of cookie boxes will be available to purchase onsite for $30.
Tickets: Preorder online, up to two boxes per order. Online preorders are limited.

Good to know

What time does the Cookie Crawl begin?

The Cookie Crawl begins at 11:00 AM, right after the Holiday Spectacular Parade, and runs until 2:00 PM.

Where do I pick up my box?

Check in at our table on Cochran Square (corner of Broad and Main Streets) to get your cookie box and your list of stops.

How much does it cost?

Preorder online for $20 per cookie box, up to two boxes per order. Online preorders are limited. A limited number of cookie boxes will be available to purchase onsite for $30.

Which businesses are participating?

The crawl includes 13 participating downtown merchants. The list of participating merchants will be posted here soon.

Who bakes the cookies?

Every cookie on the crawl is baked by Sweet Melissa's.

Preorder your box before they are gone

Join us Saturday, December 5, 2026 for The Great Middletown Cookie Crawl in Downtown Middletown.

Preorder your cookie box