Downtown Rutland
The heart of Rutland County.


The Downtown Rutland Partnership hosts annual events incuding Friday Night Live, the Downtown Rutland Holiday Stroll, Sidewalk Sales and Tree Lighting. Visit this page for a full calendar of events in Downtown Rutland, Vermont.


Annual Events

The Downtown Rutland Partnership hosts and partners on several signature events throughout the year.

 Spin Doctors, July 24, 2015

Spin Doctors, July 24, 2015

Friday Night Live Concert Series

Friday Night Live is a free outdoor concert series that takes place on Center Street throughout July. This fun and casual series draws the community together to enjoy music, outdoor dining, shopping, children’s activities and more starting at 5pm. The “Pit” parking lot on the corner of Center & Wales Streets transforms into a unique, amphitheater-like concert venue with great acoustics. Openers play in the street and headliners take the stage at 8pm. View the list of vendors and learn more about each night here >>

2018 Dates: July 13th: 8084 - July 20th: Kat Wright - July 27th: John Waite


Downtown Street Party

The end of July and start of August has marked the Annual Sidewalk Sales for years. This year, downtown will be full of fun activities as we throw a street party for the community complete with open-air market that spans from lower Center Street around the corner to Merchants Row, drawing out sale tents and outdoor dining from businesses along the way. Enjoy a variety of family entertainment as well as local artists, crafts, food vendors and live music from area musicians. View the list of vendors and learn more >>

2018 Date: August 4th, 9am to 5pm


Halloween Parade

The Rutland Halloween Parade is a historic tradition for Vermonters for over 50 years. Downtown Rutland comes alive each October with floats from merchants and organizations to get you into the spirit of Halloween! The parade has a strong superhero theme and has been the setting for a number of comic book adventures, including Batman and Thor. Read more about the history of the parade here. For details and info on getting involved, visit the Rutland Rec's Website.

2018 Date: October 27th


Downtown Rutland Holiday Stroll

 Support your local downtown shops, restaurants and venues this holiday season as they offer a special day of sales, treats, and activities in honor of Small Business Saturday. You’ll find a huge variety of gift options that are one-of-a-kind and fit for practically everyone on your list. Avoid those big crowds and get a personalized, friendly shopping experience!

New this year: Head to The Paramount Theatre at 10am for a free screening of “The Polar Express!” Santa will be in the lobby for a meet & greet immediately after, from 11:30am to 2pm.

2018 Date: Saturday, November 24th


Tree Lighting Ceremony

Santa visits us in Downtown every winter and helps to light the tree in Depot Park. Enjoy a night of caroling, hot chocolate and goodies. This is a wonderful community event that helps to kick off the holiday season!

2018 Date: Saturday, November 24th @ 5:30pm


Late Shopping Night

Dash Downtown to scoop up those last minute gifts! Participating merchants stay open until 8pm on the last Thursday before Christmas. Enjoy the holiday lights and decorated windows as you shop for loved ones, locally.

2018 Date: Thursday, December 20th


Winter Fest

The Rutland Winter Fest features a week-and-a-half of activities to get the community involved in fun in the snow and out of the winter blues. Downtown activities include Center Street Night Sledding, where the street is closed to traffic and filled with snow for tubing, and the Center Street Story Walk, where children read the pages of a book in the windows of store fronts. Other activities throughout the week include ice skating, snow sculpting, chili cook-off, broom ball, art walk, Frosty Feet 5K, snow shoeing, and more.

2019 Dates: Friday, February 15th through Saturday, February 23rd


Downtown Green Up Day

Join the Downtown Rutland Partnership and lend a hand to cleanup Downtown Rutland on Vermont's Green Up Day. Always the first Saturday in May, this is a special day in Vermont when thousands of volunteers come out in their communities for a massive spring clean up of litter. It is the largest statewide volunteer event in Vermont with over 22,000 taking part, and the only statewide Green Up Day in the United States. 

2019 Date: Saturday, May 4th

Current Events

Regional Events

 A ferris wheel spinning at the 2017 Vermont State Fair in Rutland, Vermont. Photo by Donna Wilkins.

Vermont State Fair

One of the oldest state fairs in the United States, the Vermont State Fair features amusement rides, performances, a demolition derby, races, fireworks, and more. This year's headlining musical act is Dan Tyminski.

2018 Date: Tuesday, August 14th - Saturday, August 18th


Vintage Market Days of Vermont

An upscale vintage-inspired indoor/outdoor market, Vintage Market Days features original art, antiques, clothing, jewelry, handmade treasures, home décor, outdoor furnishings, consumable yummies, seasonal plantings and a little more at the Vermont State Fairgrounds. 

2018 Spring Date: Friday, April 27th - Sunday, April 29th
2018 Fall Date: Friday, October 12th - Sunday, October 14th

 Peter Huntoon paints at Art in the Park.

Art in the Park

Now in its 57th year, Art in the Park is a set of historically-occurring fine arts and crafts festival hosted by Chaffee Art Center in Main Street Park. Find pottery, paintings, photography, woodworking, fibers, jewelry and more from Vermont craftspeople.

2018 Summer Date: August 11th & 12th
2018 Fall Date: October 6th & 7th

 Three competitors in the Xfinity Killington Cup in 2016.

Xfinity Killington Cup

A stop on the Audi FIS Ski Women's World Cup Tour you don't want to miss! Over 30,000 people converge to watch women race down the slopes of Killington Mountain, home to New England's largest vertical drop.

2018 Date: November 24th - 25th