Things to Do

Explore the Green Mountain State

The beauty of Vermont is in our diverse natural surroundings, historic downtowns and country roads winding through our and towns and villages, where the variety of shops, restaurants, theaters and galleries still dot the landscape from end-to-end of the state for your enjoyment. From can’t miss annual events to fun races for great causes, find a list of  fun things to do that in the Rutland and Killington region of Vermont below!

Rutland Vermont Energy Trail

Green Mountain Power — Solar Energy Trail

Rutland Solar Capital Initiative Enter to WIN FREE STUFF! GMP’s Rutland Solar Capital Initiative is designed to create and inspire construction of enough solar to provide Rutland with the highest solar capacity per capita of any city in New England. Details of Participation in Drawing No purchase necessary. Visit the participating merchants listed on this page. […]


Crossroad of Vermont Byway

The Crossroad of Vermont Byway follows the east-west roadway of US Route 4 that literally crosses the state’s Green Mountains from Rutland to Hartford. Travelers get a unique glimpse into the qualities that define Vermont as one of the most beautiful states in the country, finding the charm that one expects and the scenic and […]

Art in the Park, Downtown Rutland VT

Art in the Park

This year Art in the Park in Rutland, Vermont the Chaffee Art Center is celebrating its 54th annual Art in the Park!   It kicks off on Saturday August 8 and goes through Sunday August 9, 2015. Then on Columbus Day Weekend, its back again to delight leaf peeper on October 10-11, 2015. Art in the Park vendors are open from 8 […]

Vermont Open Studio Weekend

Vermont Open Studio Weekend

Don’t miss your chance to meet and chat with artists and artisans up close and personal!  The Spring Vermont Open Studio Weekend, is on May 23 & 24, 2015, and is free to all participants. It happens at hundreds of participating studios across the state of Vermont. Visit and chat with sculptors, painters, artists, potters, weavers, furniture makers, maple […]

Killington Classic & Rutland Block Party

2015 Killington Classic Motorcycle Rally - Grand Parade & Downtown Block Party

Join us for the Grand Parade Friday night, August 28th 2015, from Killington Road as motorcycles and enthusiasts gather in Downtown Rutland, Vermont for a huge block party to welcome thousands of bikers visiting Rutland and Killington from across the country for the Killington Classic Motorcycle Rally! Enjoy A Classic; The Killington Classic Motorcycle Rally […]

Georgetti Park Ice Skating in Rutland


The Rutland area is home to dozens of official parks to enjoy the outdoors, along with many swimming holes, open spaces, mountains for hiking and more! Here is a list of some of the community facilities available and waiting for you to come play outside! Five playgrounds Ten public parks (two with gazebos) 16 miles […]

Rutland Halloween Costume Parade

Rutland Halloween Parade

One of Rutland’s Largest Community Gatherings The annual Halloween Parade is also one of the most fun and impressive family-friendly things to do in Rutland!   Every year, over a hundred floats are created by organizations from the Rutland area.  See school groups, scout troops, local businesses, marching bands, political organizations, local businesses and so many […]

Vermont State Fair, Rutland VT

Vermont State Fair

Sep 5-12, 2015 marks the 170th year of the Vermont State Fair, making it one of the oldest state fairs in the United States.  Visit the midway with over 35 rides, games and concessions and enjoy the wide variety of fair food – always a highlight!  The Vermont State Fair boasts a huge array of […]

Relay for Life in Rutland VT

Relay for Life

Saturday, June 20, 2015 at the Vermont State Fairgrounds, Main St., Rutland, Vermont.  Every year, thousands of participants get together at the Vermont State Fairgrounds in Rutland, Vermont to celebrate the lives of those who have battled cancer, to inspire hope by sharing recent accomplishments and progress, and to remind everyone that while we are […]

Crowley Brothers 10K Road Race

Crowley Brothers Memorial Race

June 6-7, 2015. The Crowley Road Race Weekend “kicks off” on Saturday, June 6th from 10-4 pm, with the 9th Annual Crowley Brothers’ Annual Sport and Fitness Expo to be held at the Rutland Middle School Keefe Gym on Library Avenue. The 39th running of the Crowley Brothers’ Memorial 10K Road Race Half Marathon and […]