Lydia B.
Yelp
A true gem! It used to be located in Somerville near Tufts and was a favorite of college kids and neighborhood families, and has quickly become a Winchester staple. If you're a chocolate fan, the flourless chocolate cookies and cocoa joel ice cream are both to die for. The nutella or oreo stuffed chocolate chip cookies are delicious if you're feeling extravagant. I'm also a fan of the salted caramel and cow trax ice creams. Overall, you can't go wrong! Some pretty solid vegan and gluten free options. It's a cute place with a few tables, and there are various benches nearby in downtown Winchester if the store is full.
A tip: you can get just ice cream, a half hoagie (a small ice cream with one cookie), or a whole hoagie (a full sandwich with two cookies). The whole hoagie is fun as a concept but is somewhat impractical to eat and is a lot of food -- I would recommend just getting a half hoagie and using your spoon to scoop ice cream onto the cookie as you eat. That way you get both cookie + ice cream at once without the cookies crumbling and ice cream everywhere.