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A Halloween twist on a downtown favorite
Thursday, October 29, 2026 | 5:00 PM – 7:00 PM
The CharBOOterie Crawl brings a fall evening of food, local flavor, and Main Street discovery to downtown Middletown. Guests will make their way among five downtown stops on the west side of Main Street, enjoying a different charcuterie course curated by Sweet Dreams Confections at each stop.
Optional wine, beer, and mocktail tastings add another layer to the experience, with selections from local and regional tasting partners. Costumes are welcome, but the real focus is a relaxed two-hour route built around good food, downtown businesses, and time together.
Tickets are $35. Attendees must be 21 or older.
One evening. Five downtown stops.
Each ticket opens the door to a two-hour tasting route along the west side of Main Street:
- A charcuterie course at each of five downtown stops, curated by Sweet Dreams Confections
- Optional wine, beer, and mocktail tastings
- Time to browse and enjoy downtown at an easy pace
- A Halloween-season atmosphere, with costumes welcome
There is no stage to watch and no single room to stay in. The evening unfolds across downtown—one stop, one bite, and one distinctive Main Street setting at a time.
Olivia Walker
Editor in Chief
Five stops, one downtown evening
Five downtown businesses will make up the 2026 CharBOOterie Crawl route. Participating locations are still being finalized and will be announced as the event approaches.
Each stop will contribute a different setting to the evening, while Sweet Dreams Confections curates the charcuterie courses served along the route. Together, the stops create a reason to see more of downtown—and perhaps discover a place you will want to visit again.
Plan your evening
- Date: Thursday, October 29, 2026
- Time: 5:00 PM–7:00 PM
- Location: West side of Main Street in downtown Middletown
- Tickets: $35 per person
- Age: Attendees must be 21 or older
- Dress: Costumes are welcome
Ticket sales and the official event listing are handled through the Middletown Main Street Wix Events page. Use the button below for availability and booking.
Meet the tasting partners
Broken Spoke Winery, Harvest Ridge Winery, DdProject Wines, and Volunteer Brewing join the 2026 crawl as tasting partners. Their participation gives guests a chance to pair the food route with optional wine and beer selections, while mocktail choices keep the tasting experience flexible.
The result is a fuller evening without losing the event’s local character: downtown stops host the experience, Sweet Dreams Confections curates the charcuterie courses, and each tasting partner brings something distinct to the route.
Olivia Walker
Middletown Main Street is a non-profit organization, which will be benefitting from the sales of alcohol.