With National Ice Cream Month nearing its end, I’ve been trying to take advantage of my off days and have been venturing to towns that I haven’t been to a shoppe. Since it wasn’t beach weather, I didn’t head to the shore and instead found my maps pointed to Winchester where I landed this Chocolate Walnut Fudge cone.
Despite the fact that Cups And Cones has only been here since May, ice cream at this location has been around for nearly fifteen years. Most recently the store was called Karol’s Ice Cream And Italian Pastry until it was sold to new owner Tom Cullen earlier this year. Originally this place was Yankee Yogurt, and at some point it was also called Andi’s.
Downtown Winchester is neatly split by the train depot for the Lowell-Boston line. I parked on the green side and wandered around checking out the storefronts of this little downtown. Cups and Cones is located at the perimeter of the buildings, much further on and things get residential. Within the brick-sidewalked streets though there is an array of odd boutiques, a shoehorned CVS, a trophy shop, and even a Christian Science Reading Room.
Inside is a small shop with a checkerboard floor and a few tables, and across the street there is are four benches arranged in a square where I sat to eat. As the flavor list certainly pointed out, the ice cream here is provided by Richardson’s. This place seems to operate by getting their stuff from quality local businesses: the pastries are from the North End, the slush is Richie’s.
Knowing what to expect from the ice cream I went with the chocolate walnut fudge to fill my cone without taking any samples. The small cone was bigger than I expected, which brought me back inside afterwards for some napkins to wipe the chocolate out of my beard – whenever there is more than a single scoop, napkins are an imperative. The ice cream was nice, with the nuts and fudge really making a fun mess of things. The nuts didn’t have that freshly cracked taste that makes the best ice creams better, but this was just what I needed.
After eating a cone, I realized that I needed some real food as well. I walked around scoping out the restaurants and landed at Nelson’s Bakery. As soon as I walked inside the first thing I noticed was a freezer case full of tubs of ice cream and frozen yogurt. The source for their ice cream is Puritan from Jamaica Plain, which I was surprised by since I thought they only supplied to restaurants and not any parlors. The owner was more shocked that I had even heard of Puritan. Instead of going with another cone, I had a great ham and brie sandwich that could only have been improved upon if the mustard had not been on the same side as the brie.
Cone – kids $2.85 regular $3.80 large $4.29
Sundae – regular $5.95 large $6.49
Frappe $5.75
Cups and Cones
527 Main St, Winchester, MA 01890-2914
781 729-1735
Open year round or maybe closed for a few months in the Winter
We All Scream For Ice Cream! 
Yeah I scream for ice cream but even more I scream at your employees for wanting to get out of Dodge so badly they shut the lights off at 0:45 when I was hoping to get in before closing. Here’s a thought…….Shutting the lights off and standing in the dark like demented gnomes pretending you aren’t there and then sayin “Ohhhhhh ummmmm yeah we’re closed” when questioned suggests you aren’t too serious about doing business.
Result? I’d pull out my own fingernails before doing business with you again.
Best of luck!!!!!