A Progressive Dinner at Clifton Square & Happiness Plaza

One thing I’ve been wanting to do for a while is a Progressive Dinner. What’s that you ask?

A progressive dinner is one where you eat each individual course in a different location. Head to one restaurant for appetizers, off to a second for entrees, and a third for dessert, or add in additional stops along the way. It’s basically a traveling meal. This type of dinner outing provides the opportunity to try multiple places in one night. It also combats the tendency that we often have to rush through the meal; the travel time in between courses affords extra opportunities to chat with friends.

For this progressive dinner, I was joined by members of The Neighborhood and fellow food blog friends, Just Try It and Significantly Spicy. After discussing where to go for our progressive dinner, we decided on Clifton Square and Happiness Plaza located on Douglas in the heart of College Hill. So many great options all within walking distance. Here’s how our evening went:

Our first stop was The Flower Shop. It’s basically a waiting area for The Belmont. It’s a quaint, charming space with an old house type of vibe. People can order drinks from The Belmont’s menu as wait there for their table.

We all ordered some cocktails as we waited for our table at The Belmont. If you love cocktails, this place (and of course the Belmont) come highly recommended. Their cocktail menu is small in selection but big on flavor. I started off with the Calumet which was vodka, aperol, white peach, simple syrup, lemon juice, and orchard peach liqueur.

Soon after, our table at the Belmont was ready. It was the first food leg of our Progressive Dinner. We were able to sit in the mezzanine area that overlooked one of the coolest restaurant spaces in town.

For this leg of our dinner, we ordered everything bruschetta option they had. I also made sure to sneak one more cocktail in. I went with the Daylight which was vodka, meyer lemon, simple syrup and lemon juice. The five of us dined on bruschetta and each had our own favorites. Mine was the fig ricotta, pistachios and prosciutto.

While tabbing out, they gave us a plate of cookies to share. The snickerdoodle……marvelous.

We then used the crosswalk because safety first and made our way over to Ziggy’s Pizza.

For another round of apps on our progressive dinner, we had the Ziggy’s sample which was pretzels, cheesy garlic and Ziggy bites along with an order of wings (Ziggy’s Blend and Caribbean Jerk Dry Rub).

Everyone was a huge fan of the pretzel, but I couldn’t get over the wings. They are my top three favorite wings in town; extremely meaty, juicy and flavorful. The Ziggy’s Blend cannot be beat when it comes to sauced wings.

Around this time, many of us were hitting the struggle bus, but made our way over to Dempsey’s Burger Pub.

For the main entree leg of our progressive dinner, the five of us split two burgers and two baskets of fries. We had the Gouda Life burger special which was Wiens wagyu beef patty topped with caramelized onion aioli, two slices of smoked Gouda cheese, bacon and baby arugula on a brioche bun. Our second burger was the Bleu Burger which included Maytag bleu cheese, bacon, and shallot marmalade. For our fries, we had the duck fries and truffle fries along with every condiment known to man.

With a long night of eating already taking place, the two burgers cut into fours was more than enough for us. Hell, the basket of fries probably would have sufficed to, but we did our best to enjoy dinner. We’ve all been to Dempsey’s before and thoroughly enjoyed the food. You can’t go wrong with the truffle fries here.

For the final leg of our progressive dinner, we managed to save room for dessert and walked over to Papa’s General Store for ice cream.