The Rocheport Area Merchants Association (RAMA) is the group of shop, gallery, café, winery and inn owners who look after Rocheport’s visitor calendar. They keep a directory of the businesses in the village and put on the festivals that fill the streets with people: a chocolate walk in winter, a tasting evening in June, a market day each month of the season, a day of live music in the fall, and a candlelit holiday open house. If you want to know when Rocheport is at its best, start here.
Annual events
Chocolate Crawl, Saturday, Feb. 20, 2027. A self-guided winter walk through town, with a chocolate treat waiting at each participating shop, café, gallery and inn. Tickets are sold in advance and the number is limited. How the Crawl works.
Rocheport Stroll, Saturday, June 19, 2027. An early-evening walk through the historic village with live music and samples from Missouri wineries, breweries and distilleries, poured at stops among the local shops. The 2026 Stroll ran 4 to 8 p.m., and a ticket included a commemorative wine glass. About the Stroll.
Rocheport Live!, Saturday, Oct. 23, 2027. Free, on the fourth Saturday in October. Bands play all day at cafés, gardens, inns and the winery across town, from late morning into the night, so you can walk from one stage to the next. This year’s lineup.
Wassail Walk, Friday, Nov. 26, 2027. Free, on the Friday after Thanksgiving. Merchants pour warm spiced cider, the shops are dressed for the season, Santa visits, and the village Christmas tree is lit. Wassail Walk listing and the tradition. This year’s walk, on Friday, Nov. 27, 2026, includes a raffle basket drawing for the library’s bookmobiles; raffle tickets are $5, or five for $20.
Second Saturdays, April through October
A free, family-friendly market day on the second Saturday of each month from April to October, with a mix of regular and rotating vendors. 2027 dates: April 10, May 8, June 12, July 10, Aug. 14, Sept. 11 and Oct. 9.