June 2025 Vermont Events: Festivals, Live Music & Family Fun

Introduction

Summer in Vermont is synonymous with connection, community, and celebration. For locals and visitors alike, June marks the beginning of a vibrant season filled with festivals, live music, and outdoor gatherings that bring people together. As a local Burlington-area realtor, I know firsthand how valuable these events are—not only for creating memories but also for forging lasting relationships in the community. Whether you’re looking to meet neighbors, explore new places, or enjoy Vermont’s small-town charm, this curated calendar offers something for everyone.

June 4 – Trivia Night with Top Hat at Sparky’s Bar & Grill

Ready to test your knowledge and enjoy a fun-filled evening with friends? Head to Sparky’s Bar & Grill in Essex Junction on June 4th for Trivia Night with Top Hat Entertainment. This weekly event challenges participants with rounds of questions and offers prizes to the sharpest minds in the room. It’s a perfect way to kick off the month, make new connections, and maybe even prove you’re smarter than a 5th grader!

• • Location: 4 Lincoln Place, Essex Junction

• • Time: 5–7 PM

• • More Info: Event Link

June 7 – Round Church Concert in Richmond

Enjoy the soothing sounds of bluegrass in one of Vermont’s most iconic venues. On June 7th, the historic Old Round Church in Richmond will host a concert featuring Forest Station, blending musical tradition with community spirit. Sponsored by the Richmond Historical Society and Northfield Savings Bank, this evening promises an unforgettable auditory experience in a charming, acoustically rich setting.

• • Location: 25 Round Church Rd, Richmond

• • Time: 7 PM

• • More Info: Event Link

June 7 – Twilight Block Party in Burlington

On the same evening, Burlington’s City Hall Park lights up with the Twilight Block Party, a downtown extravaganza combining the best of the Twilight and BTV Markets. This lively event features local music, a variety of vendors, art activities, and delicious bites for the whole family. It’s a great opportunity to immerse yourself in Burlington’s creative spirit and connect with residents and local artisans.

• • Location: City Hall Park, Burlington

• • Time: 4–8 PM

• • More Info: Event Link

June 13 – Last Day of School Party at Judi’s Ice Cream

Celebrate the start of summer break with a sweet treat! On June 13th, Judi’s Ice Cream in Williston is hosting an all-day Last Day of School Party. Students who visit with an adult receive a free kid-sized creemee, kicking off summer vacation with joy and flavor. It’s a delightful way for families to reward their children and enjoy a relaxed outing together.

• • Location: 373 Blair Park Road #103, Williston

• • Time: 11 AM–9 PM

• • More Info: Event Link

June 20 – Winooski Juneteenth Celebration

Commemorating a pivotal moment in American history, the Winooski Juneteenth Celebration brings together music, food, and education on June 20th. Hosted at Winooski Rotary, this event honors the emancipation of enslaved African Americans with performances, community discussions, and festivities. It’s a meaningful occasion to reflect and celebrate progress while enjoying the vibrant community vibe.

• • Location: Winooski Rotary

• • Time: 5–8 PM

• • More Info: Event Link

June 21 – Strawberry Festival in Colchester

Strawberries and sunshine await at the Strawberry Festival in Colchester on June 21st. This charming family event features pony rides, a magic show, balloon twisting, and crafts for kids. With Charlie Rice as MC and a lineup of food vendors offering strawberry fudge and pizza, it promises to be a delightfully sweet way to spend the afternoon.

• • Location: 277 Lavigne Rd, Colchester

• • Time: 11 AM – 4 PM

• • More Info: Event Link

June 21-22 – Vermont Renaissance Faire in Essex

Step back in time at the Vermont Renaissance Faire, taking place June 21–22 at the Champlain Valley Expo. Enjoy a weekend packed with medieval flair, from jousting tournaments and aerialist shows to local artisans, mead, and cider makers. Don your best costume or come as you are—this event brings the 1500s to life with entertainment for all ages.

• • Location: Champlain Valley Expo, Essex

• • Time: 10 AM – 6 PM

• • More Info: Event Link

June 27-29 – Stowe Balloon Festival

Experience a sky full of color at the Stowe Balloon Festival, happening June 27–29 at the scenic von Trapp Family Lodge. This three-day celebration includes hot air balloon launches, live music, food trucks, and artisan vendors, making it a perfect weekend getaway for families and adventurers alike.

• • Location: 700 Trapp Hill Rd, Stowe

• • Time: 5–8 PM

• • More Info: Event Link

June 28 – Kick It Into High Gear at Essex Experience

Close out the month with high energy at the Kick It Into High Gear celebration on June 28th. Held at Essex Experience and benefiting the Vermont Foodbank, this lively community gathering offers live music starting at 4 PM, family-friendly activities, and plenty of delicious local BBQ and craft beverages. It’s an excellent opportunity to have fun while giving back to a vital cause.

• • Location: 21 Essex Way, Essex Junction

• • Time: Starts at 4 PM

• • More Info: Event Link

Conclusion

June in Vermont offers more than just sunshine—it’s a celebration of community, connection, and local culture. Whether you’re a lifelong resident or a newcomer looking to make connections, these events are the perfect way to get involved, have fun, and experience the spirit of the Green Mountain State. As a local Burlington-area realtor, I always encourage my clients and neighbors to participate in these gatherings to discover the heart of our towns and the warmth of our people. See you out there!

Frequently Asked Questions

1. Are these events free to attend?

Many events are free or low-cost, though some may have suggested donations or vendor fees. Always check the official event page for specifics.

2. Which events are best for families with young children?

The Strawberry Festival, Judi’s Ice Cream Party, and the Vermont Renaissance Faire offer kid-friendly activities and entertainment suited for all ages.

3. Where can I find parking information?

Most event pages on Facebook or the event’s official site provide parking tips. Arriving early is always recommended for popular events.

4. How can I support local businesses during these events?

Shop from local vendors, dine at food trucks, and follow small businesses on social media. Your support makes a big impact!

5. I’m new to the area—how can I meet people at these events?

These events are excellent networking opportunities. Attend with an open mind, join group activities, and don’t be afraid to strike up a conversation!