Sometimes you forget how bad rush hour traffic can be in the city. I kept readjusting my destination based on how bad things were moving. Instead of finding my way to soft serve in Saugus, I found a parking spot in City Square and decided to indulge myself with a Sorbet Trio after shelling out so much cash for my car this week.

Olives was Todd English’s first restaurant. Begun in 1989, it’s the one that launched him to celebrity status. This isn’t the original location, it moved down the street, and has expanded to locations in New York and Las Vegas. There are eight other restaurants that fall within English’s domain, so it’s rare to find him manning the brick oven here.
Located on the Freedom Trail, Olives is almost in the shadow of the Zakim Bridge. Actually if you look at maps of this area as late as the 1980s, you’d find what is now City Square mostly served as footing for pilings that held highways aloft. Now there’s a great little park with fountains and monuments, and thriving businesses nearby. This neighborhood is quite urbane, and the presence of a five-star restaurant certainly helps that outlook.
Now Olives is not a place most people think of when ice cream is the goal. With neo-Mediterranean cuisine, even the most regular patrons often think of the desserts as an afterthought. I opted for a seat at the bar since I was on my own, but they can accommodate groups of up to a dozen, though I would recommend making reservations. Attempting to not look too conspicuous, I started with a Woodford Reserve on the rocks and ordered their version of a bar pie – crispy duck, blue cheese and figs grilled on flatbread.
The dessert menu incorporated their homemade vanilla ice cream into a couple of the dishes, but it seemed as though the sorbet trio was most directly in my wheelhouse. Served in a martini glass with a sprig of mint, there were scoops of coconut lime, mango and cantaloupe sorbet, with a couple of thin biscotti to keep the palate clean. The coconut lime was very subtle with the two flavors both seemingly trying to step back and let the other take control; ultimately I had my biggest bite with the mint too and that united the flavors (the ice cream version of this at Jake’s was superior). The mango sorbet had the rich full color of the fruit, but the flavor was also tempered and lacked the textural unity that Coop’s had with the same flavor at the Somerville Showdown. The cantaloupe was what I was hoping for when I spent $9 on this dessert: sweet and delectable, with the fruit pieces and the sorbet combining in a way that it was tough to know which to give credit for which bursts of taste.

For as indulgent as this trip was, it was also one of the most fascinating conversations I’ve been involved with in ages. Being seated between a former basketball player and a gorgeous short single woman and her taller but taken friend led to some frank discussions that began when he realized that I actually had larger feet than he did. Even if you let your mind wander to its darkest corners, you might not approach the things that were spoken loudly. Despite all of that and her small stature, her honesty and pragmatism left me with the sort of smile that makes me hope I find her again on an ice cream run.
menu varies; Sorbet Trio $9
Olives
10 City Sq, Charlestown, MA 02129-3740
617 242-1999
Open year round
Monday-Friday: 5:30p-10p, Saturday 5p-10:30p, Sunday 5p-9p