Winter Progressive Dinner: Downtown Chattanooga

Chattanooga’s impressive food scene can make deciding where to dine out difficult. Experience more of what our local chefs have to offer in a single night with a progressive dinner experience instead. Here’s an itinerary that will keep your travel between courses to under a mile.

Hello Monty for a Progressive Dinner in Chattanooga

There’s a story that circulates among Southside businesses: Nearly 100 years ago, a local businessman named B. Rush Montgomery, known as Monty to his pals, stood on what would one day be Main Street and predicted the future of the Scenic City. Someday, he announced, Chattanooga would be home to 1 million people. Chattanooga natives Rob and Clay Gentry pay homage to Monty’s enthusiasm with their West Main Street restaurant, Hello Monty. Co-founders of Big River Grille & Brewing Works and founders of The Blue Plate, the Gentrys have created a space that is quaint and minimalistic with a quirky charm. They also brew their own beer. For the best prices at the bar, Monty Hour pricing** includes $4 Dynamo beers and $15 carafes of draft cocktails. Thursdays this winter are Break Even Bottle Nights; at 5 p.m., the bar will open a top-shelf spirit or wine and pour it “at cost” until it’s gone. 

This is the only bar in Chattanooga with traditional beer engines serving cask-conditioned ales. The Dynamo Helles is a Munich-style pale lager, and the Dynamo IPA is hops-heavy with a hint of citrus. Cocktail options include an Old Fashioned, a Whiskey Sour, and The Mexican Firing Squad, which is made with tequila, lime, house grenadine, and hellfire bitters. For your starters, check out the Blistered Tomato Toast, topped with shaved country ham, tomato compote, goat cheese, and spiced honey and the Cast Iron Beer Cheese Dip made from a dynamo lager, pickled banana peppers, and oven-roasted garlic cloves – served with a grilled Neidlov’s country loaf. Seating includes an outdoor patio wrapped for warmth in the winter.  

**Monty Hour is hosted Wednesday through Friday from 3 p.m. to 6 p.m. and Saturday and Sunday from 11 a.m. to 4 p.m.

Two Ten Jack Chattanooga Progressive Dinner.

A Japanese-inspired pub located downstairs in Chattanooga’s Warehouse Row, Two Ten Jack offers a comfortable “izakaya experience,” a place where local culture and Japanese culture merge. The 2-10-salad is made with cabbage, radishes, peas, bacon, and eggs. The seaweed salad has hijiki, wakame, tosaka, and a miso vinaigrette. Salads aside, locals know Two Ten Jack for its warm, filling ramen bowls. The tonkotsu is a pork broth with chashu (braised pork belly), menma (bamboo shoots), kikurage (mushroom), baby vidalia, mayu (a burnt garlic oil), and a soft egg. The yasai shoyu is a vegetable broth with burnt corn, greens, red pickled ginger, and garlic oil.

Tupelo Honey Chattanooga Dinner recommendation.

Also located in Warehouse Row, Tupelo Honey touts Carolina-mountains-inspired “Sunday best” Southern food and is known for sourcing local, in-season produce and proteins raised with respect. Partnering with purveyors Adluh Flour, American Shrimp, Beeler’s Pure Pork, and Imladris Farms, among others, Tupelo Honey executive chef Eric Gabrynowicz is a four-time James Beard Award Semifinalist. In Chattanooga, the 2023 winter menu includes the Grilled Salmon and Creamy Quinoa, served with roasted carrots and cauliflower, smoky harissa sauce, and chives. The Harvest Bowl has roasted garlic and cumin quinoa, sauteed cauliflower, carrots, shaved brussels, sprouts, radish, fennel, broccolini, and a roasted red pepper romesco sauce. Year-round favorites include the bone-in fried chicken (with waffles, if you like) and the Tupelo Shrimp & Grits, which includes sustainably wild-caught white gulf shrimp, chorizo pork sausage, peperonata, creole sauce, scallions, and heirloom grits with goat cheese.

Easy Bistro Progressive Dinner recommendations.

With Louisiana-native executive chef Erik Niel at the helm, Easy Bistro & Bar is located in West Village. After studying psychology at the University of Texas at Austin, Niel attended Johnson & Wales Culinary School in Vail, Colorado, and began his work in restaurants as a manager at Southside Grill. There, he met his wife Amanda. The pair then spent time working at local fine dining restaurant St. John’s, then opened Easy in 2005. While it’s ultimately the place where seafood shines in the Scenic City, the restaurant’s bright interior (think blues, whites, and golds), beautiful plating, and friendly atmosphere make it a perfect stop for dessert. This winter’s dessert menu includes an Apple Crisp, made with oats, pecans, and caramel cream, and a Coffee Panna Cotta with chocolate espresso beans.

Late Night Drinks at Stir Chattanooga for a winter progressive dinner.

Located in the Chattanooga Choo Choo complex, STIR is where you’ll find one of the most extensive drink menus in town. The 350 options are organized by Beer & Wine, Craft Cocktails, Craft Cocktails on Draft, Barrel-aged Cocktails, Bourbon, Rye, Tennessee Whiskey, Imported Whiskey, Gin & Vodka, Agave Spirits & Rum, Cordials & Other Spirits, and Non-Alcoholic Beverages. The atmosphere is energetic, as it’s open until midnight and a convenient walking distance from The Comedy Catch, Kinley Chattanooga Southside, Songbirds Guitar & Pop Culture Museum, Main Terrain Art Park, ‘80s and ‘90s dance bar Regan’s Place, and several local breweries. At STIR, each cocktail is poured over dense artisanal ice that has been frozen, cut, and shaped by hand. The slow melt ensures that your drink stays fresh. The syrups and bitters are made in-house as well, and the restaurant prides itself on procuring rare liquors to add to the menu.

At STIR, the Whiskey Bramble is a new twist on an Old Fashioned and includes cherry Amarascata, lemon, and orange blossom water. The Slack-Jawed Jezebel is a bourbon blended with house-made ginger cordial and lemon curd. This winter, rare bourbon & rye specials include a 1792 Small Batch, Barrel Bourbon Vantage, and Kentucky Owl Confiscated. Cocktail specials for February 2023 include the Three Piece Suit, a martini made with Reposado Tequila, Oloroso Sherry, sugar, and orange bitters, while Luv-U-Berry Much is a vodka cocktail with St. Germain, herbal liqueur, lemon, mint, and strawberry. 

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