Check out this What To Do in Rutland, Vermont trip by AFST on Steller!

What To Do in Rutland, VermontRutland, Vermont, blends history, art, and nature. Downtown charms with murals, sculptures, and the Paramount Theatre, while nearby parks and Pine Hill trails offer outdoor adventures. Seasonal events and local markets showcase the city’s vibrant cultural and natural life.AuthorsAFST
DestinationsRutlandItinerary

Eats

Loose Loona Gifts and Teahouse
A notable spot is Loose Loona, a specialty shop that combines retail with a tea house experience.
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Jones Donuts & Bakery
Jones Donuts & Bakery is a classic Vermont spot for sweet treats and coffee. Don’t skip their maple-glazed donut—rich, sticky, and perfectly paired with a hot cup of coffee for a true local experience.
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Roots the Restaurant
Roots is a farm-to-table spot highlighting local Vermont ingredients in creative dishes. Try the pan-seared trout—fresh, flaky, and perfectly seasoned, showcasing the best of the region’s seasonal produce and flavors.
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Things To Do

Rutland Downtown Historic District
The heart of Rutland, Vermont, beats in its lively Downtown Historic District, full of charming architecture, beautiful public art, and small businesses. The downtown features buildings dating back to the mid-1800s, reflecting the city's rich marble heritage.
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Paramount Theatre, VT
The striking facade of the Paramount Theatre, built in 1913, is an iconic structure that hosts performances and events, enriching community life.
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Carving Studio & Sculpture Center
Carving Studio & Sculpture Center is a hands-on art hub where visitors can try woodcarving, pottery, or bronze casting. Try a beginner carving session—you’ll leave with a small, personal piece and a real sense of accomplishment.
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Wonderfeet Kids' Museum
Wonderfeet Kids' Museum is an interactive play-and-learn space designed to spark curiosity. Don’t miss the hands-on science exhibits and creative art stations—perfect for kids to explore, experiment, and leave a little mess behind.
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Rutland Free Library
Rutland Free Library is more than just books—quiet reading nooks, community events, and local history archives make it worth a stop. Check out their rotating local author displays for a taste of Vermont storytelling.
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Vermont State Fair
Rutland offers a lively selection of local events that strengthen community bonds and attract visitors from afar. One of the most treasured traditions is the Vermont State Fair, held every August. This yearly celebration features agricultural displays, carnival rides, and tasty local food, making it one of the oldest and most cherished state fairs in the U.S.
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Rutland County Pride
In June, the Rutland County Pride Festival brings the community together with music and performances, promoting diversity and inclusion.
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Whoopie Pie Festival
The Whoopie Pie Festival in September celebrates the famous dessert, highlighting local bakeries and sweet treats.
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Chaffee Art Center
Chaffee Art Center showcases local and regional artists in a historic downtown building. Stop by during an exhibit opening to meet the artists and try their art workshops—perfect for hands-on creativity.
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Outdoors

Pine Hill Park
Pine Hill Park, located just two miles from downtown. This park covers 325 acres and features 16 miles of trails suitable for mountain bikers, trail runners, hikers, and snowshoers. Visitors can enjoy breathtaking views of the surrounding Killington and Pico mountains, making Pine Hill Park a must-visit for anyone eager to immerse themselves in nature.
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Depot Park
Another great spot is Depot Park, located near the Rutland Amtrak station. This park features lovely gardens and hosts the Summer Farmers Market, providing a charming place to relax or savor local produce.
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Center Street Marketplace Park
For outdoor dining, Center Street Marketplace Park creates a lively atmosphere with events and dining options at the local restaurant Roots. Whether you're seeking an invigorating hike or a tranquil picnic, Rutland offers plenty of options for outdoor lovers.
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