Things to do in Rutland this Summer

Staying busy in the summer is never a difficult task in Rutland County.

With a plethora of brew fests, outdoor concerts, farmers markets, and beautiful Vermont hiking trails, residents and visitors of Rutland find their schedules filled with exciting ways to spend their summers.

Serving as a pre-vacation celebration, NeighborWorks is hosting Rutland’s second annual Summer Festival.  The festival will feature free food, live music, face painting, and bike races with prizes. What better way to help the kids release some energy before returning they return to school to wrap up the academic year?

The month of June will see an influx in organized activities throughout the county.

Mountain Biking

Bicyclists in the area looking for a unique way to experience biking won’t want to miss out on Killington Resort’s Vermont Bike and Brew event. This event will feature three days of biking, drinking, and socializing at other enticing activities hosted by this event.

Rutland Recreation’s mountain bike series Droopy Pedal is back to offer fun and fitness for all ages and ability levels on June 20, July 18, and August 15. A great way to track your progress throughout the summer!

Killington Mountain Bike Club is back with their Bike Bum races. It’s a ten-week local race series that’s mostly about fun – as long as you can balance on two wheels, you’re in. For $25 a person or $100 a team, you’re entered into 10 Wednesdays of races followed by after-parties, as well as the opportunity to win great prizes.


Once July rolls in, Rutland will be host to concerts by the Rutland City Band in Main Street Park every Sunday evening, with the same park featuring concerts by various artists every Wednesday evening throughout the summer.

For a Sunday evening change-up, Rutland residents and visitors can make the short trip to neighboring Poultney to enjoy Band Concerts on the Green at the East Poultney Green.


Independence Day

Rutland’s Chamber of Commerce will ring in Independence Day on Sunday, July 2, with the county’s largest fireworks display, starting at 9:45 pm at the Vermont State Fairgrounds. On June 30 & July 1, people within Rutland County can travel to nearby Brandon or Killington to enjoy their exuberant parades and festive community activities, including picnics, barbecues, raffles, and games.

Downtown Rutland

Hops on Top will showcase 18 craft and micro breweries on top of the LAZ parking deck in Downtown Rutland. Sample beer while overlooking the city, listening to live music, and enjoying appetizers from Rutland’s own Roots the Restaurant.

Friday Night Live is returning this July with an impressive line up of bands. On July 14, 21, and 28, make sure to be in Downtown Rutland. Center Street will be closed to traffic and become a Church Street-like open market and “the Pit” will become an amphitheater. These are evenings not to miss.

National Night Out is an annual Rutland tradition. The new city pool is under construction this summer, so the community event will take place at Giorgetti Athletic Complex on Tuesday, August 1 from 4-7 PM. There’ll be a slip n’ slide, TWO bouncy houses, food on the grill, and a scavenger hunt – all for free!

Sidewalk Sales take place on Center Street and Merchants Row in Rutland on August 4 & 5. This 2-day open-air market draws out sale tents and outdoor dining from businesses along Center Street. Enjoy a variety of family entertainment as well as local artists, crafters, food vendors and live music from area musicians.

Outdoor Farmers Market

Rutland City features a year-round, twice-weekly farmers market filled with handmade crafts and homemade foods.

The Wednesday 3-6  PM and Saturday 9-1 PM market moves outside to Merchant’s Row during the warmer months, and then transfers just a few blocks away to an indoor location during cooler months.

This farmers market has a truly impressive array of products for purchase- you don’t want to miss out on this experience!


In addition to the farmers market, Rutland County is a wonderful location from which to enjoy nearby hiking and mountain biking trails. Keeping up with Vermont’s idyllic countryside, Pine Hill Park, Bald Mountain Loop Hike, and the Canty Trail all offer beautiful trails with varying levels of difficulty for hikers of all experience levels to enjoy.

Whether you’re interested in moving to Rutland, or if you just want to visit for a short time, you will never be at a loss for exciting activities that provide you with the authentic Vermont experience.

There is no other place that can offer the same sprawling mountain views, rambling trails, and exciting community events.

Make sure you make Rutland your next vacation hotspot- you may fall so in love with us that you won’t want to leave!