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. Interested in sponsoring downtown events? Check out our 2019-2020 sponsorship package.


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. Center Street transforms into a unique, amphitheater-like concert venue with great acoustics. Headliners take the stage at 8pm. Vendor applications are now closed. See you next year!

2019 Dates: July 12th, 19th & 26th from 5 to 8pm


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. Vendor applications are now closed. See you next year!

2019 Date: Saturday, August 24th from 9am to 4pm

Center Street Marketplace Park in Downtown Rutland, Vermont.

Movies in the Marketplace

Grab lawn chairs, blankets and the whole family and head to Center Street Marketplace Park for free movies on the green. Rutland Recreations present free outdoor movies once a month at 8pm on Saturdays in the Summer.

July 20: The Sandlot / Aug 24: Diary of a Wimpy Kid / Sept 28: Rio / Oct 19: Night at the Museum


Vermont Great 2-4-6-8K

Rutland Regional Medical Center presents the Vermont Great 2-4-6-8k Run & Walk - a fun event for all fitness levels - each September. Pick your own loop distance and enjoy the Green Street Challenge afterward! A portion of Center Street will turn into a green parklet for children and families to enjoy.

2019 Date: Saturday, September 21st


Fall and Spring Sip + Shops

Taste Vermont spirits, brews, ciders, wines and more while exploring Downtown Rutland’s unique, locally-owned retail stores on from on a Thursday evening. Tickets are $13 in advance and include a complimentary tasting glass and entry to all locations. Finish the whole tour and enter to win a prize!

2019 Date: Thursday, October 3rd from 5 to 8pm


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.

2019 Date: Saturday, October 26th at 6:30pm


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!

2019 Date: Saturday, November 30th from 10am to 6pm


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!

2019 Date: Saturday, November 30th at 5:30pm


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.

2020 Dates: Saturday, February 15th through Sunday, February 23rd


Shiver Me Shamrocks 5K

Kick off St. Patty's Day by running or walking in the 5th annual Shiver Me Shamrocks 5K on March 17, 2018 at 1pm. After your run, get hydrated and stay for the post-race party at The Hop’n Moose downtown. There will be raffle drawings, music, drink and food specials and lots of fun. Even if you aren’t running or walking plan to stop down and celebrate! Contact Heritage Family Credit Union to get involved.

2019 Date: Saturday, March 17th


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 from 10am to Noon

Regional Events


Killington Wine Festival

The Killington Wine Festival offers three days of wining and dining in the beautiful Green Mountains - what could be better than that? Enjoy wine tastings at Killington Peak, in some of Killington's finest restaurants, and at Vermont's #1 Public Golf Course. Events for the weekend include live music, special deals, and the signature event of the summer.  

2019 Dates: July 19th - 21st

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 every August.

2019 Dates: August 13th - 17th


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.

2019 Dates: August 10 & 11 & October 12 & 13

Three competitors in the Xfinity Killington Cup in 2016.

Killington World 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.

2019 Date: Nov 30th - Dec 1st