7 Restaurants in Westport, CT You Need to Try This Winter

I don’t know about you, but I know that when I’m at school I don’t get to eat out at nice restaurants as often as I’d like to. My meals typically consist of whatever is at the grocery store that fits my budget while still filling me up. So when I’m wined and dined by my enthusiastic parents, I can’t help but be elated…and perhaps inflated. My hometown, Westport, CT, is the best place to do this.

In the past five years, Westport has had an insane number of new restaurants open up. Because there are so many and I’m only home for a short while, it’s very important that I make it to all my favorites. Food’s the best part about the holidays, right?

So, with that, here’s a list—in no particular order because I obviously can’t play favorites—of some of my favorite Westport restaurants I will most definitely be hitting up this holiday season.

If you don’t like Brussels sprouts, then you’ve never tried the shaved Brussels sprout salad at Harvest Wine Bar. The salad consists of shaved Brussels sprouts on top of a parmesan risotto cake with truffle vinaigrette—I know, you’re drooling already.

#SpoonTip: If you’re into delicious Brussels sprouts, check out this Spoon recipe that includes Brussel sprouts, cheese, and prosciutto.

While the Brussels sprouts are most definitely a must-try, their farm-to-table menu also offers lobster mac and cheese, steak tartare, ricotta gnocchi, charred octopus, wood fire hanger steak, and plenty more rockstar options.

Located near the Westport Train Station, Harvest Wine Bar is the perfect spot for both lunch and dinner. Whether you’re looking for a casual stop before heading into NYC or a romantic date night, Harvest Wine Bar won’t disappoint.

Spotted Horse is a quintessential New England tavern with a modern take on all your favorite comfort classics. With wrought iron lighting fixtures and dark wood beaming, the Spotted Horse is the intersection of downtown meets down-home—just like the menu itself.

In case you’re interested in carbo loading (as I often am), here are two dishes that pack in the flavor…. and most likely the pounds.

First, I highly recommend the Spotted Horse Pasta with house-made rigatoni, toasted tomatoes, fresh mozzarella, garlic, and basil. You can then add sausage, grilled chicken, or shrimp. If you want my opinion, I’d opt for the sausage, but we’ve already established calories don’t count when I’m home.

Second, the Arthur Ave spring roll. It consists of a meatball with mozzarella fresca, provolone, basil, and a san marzano dipping sauce, what more could you want? Meatballs are a favorite even when not fried, so this really just amplifies the experience.

Usually food has to be the focus for a restaurant to be a favorite, but the ambiance and aesthetically pleasing Insta opportunities make Terrain Garden Cafe worth the visit. 

Dishes come served on wood planks, accompanied by drinks served in mason jars. Visits during the holiday season are particularly picturesque while dining among the twinkle lights and frosted trees.

If you’re looking for a dish recommendation here, my favorite is the grilled portabella sandwich, which is vegetarian friendly. The sandwich is served on a ciabatta roll with roasted red peppers, goat cheese, and house cut fries. Even the most ardent meat eater would have a hard time turning this down.

Bartaco is not your typical taco joint. Located right on the Saugatuck River, Bar Taco is the perfect combo of views, good eats, and a preppy wait staff. The outdoor space has heatlamps for cool summer nights—though on this visit that probably won’t cut it.  

The menu doesn’t just have your average steak, chicken, and pork taco options, but a slew of “sophisticated” options are available: Baja fish, pork belly, chorizo, falafel, portobello, fried oyster, sesame ribeye, mahi-mahi, and duck, just to name a few. Yes, I probably didn’t need to tell you half the list, but I got excited and once you nom on Bartaco’s eats you will feel just the same.

Want to learn more about Bartaco? Take a closer look at why it’s the best taco joint. 

You are happy the moment you arrive in the parking lot up until the moment you basically lick your plate clean. The Pearl at Longshore gives you the complete Westport experience. The view of the Long Island Sound combined with their steak frites and béarnaise butter-covered fries is pretty hard to say no to. Not that I need to sell you more, but it also comes with a side of black truffle sauce or red chimichurri sauce.  

Even though it’s winter time, The Pearl keeps up with Westport’s beachy atmosphere. If you take a bite of their Hummock Island oysters while watching the sun set over the beach (either in real life or in your Snapchat feed, whichever you prefer), you’ll almost forget that it’s sub 30 degrees. 

If you can’t decide if you want to go for the the classic (and basic) Margherita pizza or the adventurous pizza with cured pork, black truffles, and egg, then head to Tarry Lodge since they offer both. 

The Italian restaurant was rated as one of Connecticut’s Best Pizzas in the state by Connecticut Magazine, which means I shouldn’t have to say more more to convince you… but I will.

It has all the classic Italian options, so you really cannot go wrong. I usually start with the pork belly (because who says no to pork belly?), then order tagliatelle bolognese (it has the best sauce and is easy to pronounce compared to other Italian sauces). If I’m feeling somewhat healthy, then I’ll order the eggplant parm (if it’s covered in melted cheese is it still healthy?).

While all of my suggestions have menus that primarily consist of steak, pasta, and large amounts of cheese, there are healthy (and delicious) options in Westport too. 

Green and Tonic opened up within the last year in Downtown Westport where Crumbs Bake Shop used to be. It’s both a restaurant and mini market of sorts. You can order things like pomegranate kale salads, sunflower seed tuna wraps, and raspberry chia pudding bowl for either there or to-go.

To keep up with the whole juice fad, they sell nine different types of smoothies. The “Zenergy” consists of matcha green tea, banana, spinach, almond butter, coconut milk, cinnamon, and bee pollen. If the concept of drinking something green throws you off a bit (which it does for me), then go for the “Berry Garcia” which is made up of hibiscus tea, açaí berry, strawberries, blueberries, B12, banana, and hemp seeds.

#SpoonTip: Feel like making one yourself? Check out this green smoothie recipe. 

They also have an entire pantry section you can stock up on for when you head back to school .

Once I manage to eat my way through Westport’s greatest spots, I’ll snack (no that’s too modest, I think chomp is a better word choice) my way through Fairfield. If I follow this list of recommendations, I think my stomach, Snapchat followers, and honestly my soul will be happy.