2026 Girl Scout Cookie Walk & Wine Pairing

Who doesn't LOVE Girl Scout Cookies?!

Come join us in historic downtown Middletown for a delicious wine and cookie walk!

After checking in at the Windamere, you will walk to local shops, eateries and establishments to get different Girl Scout cookies and an optional wine pairing.

"DORA Cookie Stops" will have a specially selected $3 wine pairing available for purchase. Girl Scout cookie in one hand......paired wine in another.......does it get any better?! (The Downtown Designated Outdoor Refreshment Area will be in effect, allowing you to sip and stroll between stops!)

As an added bonus, there will be a "Cookie Monster Scavenger Hunt". Find the hidden "cookies" in Downtown businesses and redeem your passport back at the Windamere before you leave for a FREE box of Girl Scout Cookies to take home! We can't promise you will burn more calories than you consume, but it will be a fun-filled night for cookie and wine lovers.

This event serves as a DMI and DORA distrtict fundraiser to benefit DMI and our local DORA businesses! So by supporting this event you are supporting local!

How it Works: Check-In will begin at 12 p.m. at the Windamere, located at 2 South Main St. in downtown Middletown. It is here that you will trade your ticket for your cookie tasting map! The 9 cookies (and 9 wine pairings) will be located inside various local businesses & buildings throughout downtown Middletown. Wine pairings will be paid directly at the stop ($3 each) or full glasses will be available for purchase as well. There is a bit of walking involved, so make sure you wear comfortable shoes, but have no fear- this is a cookie event, not a fitness event! The hours of the event are 12 p.m. to 4 p.m, you may check-in anytime during this time frame.

Tickets: $25 and include 9 Girl Scout cookies as well as a box (your choice) of Girl Scout cookies to go home IF you complete your passport! Don't forget! You also have the opportunity to purchase a specially selected wine pairing at each cookie stop. 21+ Cheers!

FAQs:

Is there a minimum age requirements for the event?

No! The Girl Scout Cookie Walk & Scavenger Hunt is for all ages. Bring the whole family or your Wine Tribe! However it is wine focused so if you are interested in purchasing the wine pairings at each location, you must be 21+. You will need to show ID so please bring valid ID with you.

What are my transportation/parking options?

There are multiple free parking lots in and around downtown Middletown, including limited free street parking on Central Avenue and Main Street.

Is this event rain or shine? Girl Scout Cookies & Wine taste delicious in any weather so the walk will go on rain, snow or sun!

How can I contact the organizer with any questions?

Feel free to reach out to us anytime at [email protected]

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Host or Publisher Downtown Middletown Inc.