Best Comfort Food Restaurants in Rutland, Vermont

Always delicious, kind waitstaff. Perfect place to go before a show at the Paramount.

The folks at Long Trail Brewing Company go out of their way to make you feel welcome and bend over backwards to make sure you have the best dining experience possible. For a tavern that started as an extension of the brewing company, they have a relatively extensive menu, including options for people who might want to eat a bit healthier or have special dietary preferences or needs, as well as delicious pub-food offerings like Wagyu burgers, cheesesteaks, and chili dogs. They rotate the regular menu frequently to keep it seasonal and fresh for the regulars, but also have fantastic weekly specials. The restaurant is next to a river, so the summer outdoor seating options are delightful, with a path leading right down to the water. They are also extremely dog-friendly, with big comfy flannel dog beds and metal water dishes that they will set up next to your outdoor table. The staff will take turns coming out to meet your dog and seem truly happy to have you and your dog there. The wait staff is incredible, but if you are lucky enough to get Allie, you have met the best waitress in Vermont, if not the United States. Possibly the world. She is the kindest, most patient, and most generous server I have ever met, and she truly treats you like friends and family. She has never forgotten a single item or order, remembers your preferences if you are a return customer, and has no problem modifying an order or suggesting something from the menu based on your preferences and her own experiences. I have never had a bad experience with any of the waitstaff, and they are all amazing, but Allie deserves a special shout-out for her incredible customer service and generosity of spirit. I live over an hour away in central Vermont, but the Long Trail Brewing Company is a place that I have no problem driving an hour to, for both the food and the incredible staff. You guys are the best!

We had an incredible anniversary dinner at Barrows House. It was a quiet Monday. Scott was our server and he was prompt, attentive and kind. The food was fantastic and well timed. We thoroughly enjoyed our appetizer - duck confit arancini, our entrees were the halibut and the rack of lamb, we shared the almond creme brulee for dessert. Everything was perfectly cooked, well seasoned and absolutely delicious. Andrew was the bartender and we enjoyed chatting with him while we had an after dinner cocktail at the bar. We look forward to going back the next time we are in the area!

We had a lovely Mother's Day brunch at Pearl's Place. It's homey but spacious, with many choices of seating, including outdoors and by the fireplace. Our server was friendly and attentive. Both adults and young adults found food they enjoyed--from salads to strawberry shortcake. Thank you!

Charity’s has always been our go-to on the Killington Access Road.