Highlands is one of those places where spring weekends fill up fast. Between music festivals, food and fashion events, classic cars and mountaintop art, hotel rooms and vacation rentals are in high demand. If Highlands is on your list for spring 2026, now is the time to start planning so you can choose your favorite stay, lock in tickets and have a mountain escape to look forward to.
Bear Shadow Music Festival
May 29–31, 2026
A three day music festival set against blue ridge peaks and spring skies. Bear Shadow brings a nationally recognized lineup, outdoor performances and experiences that connect music, nature and community. Tickets go on sale December 11 at noon EST, so this is the first date to circle if you want Bear Shadow to be the heart of your trip. Be sure to sign up for email or text alerts on their website, so you can snag tickets before they sell out!
Plan your getaway around these marquee events
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High Style: A Celebration of Art, Cuisine, Fashion and Music
May 16, 2026
A full day of Highlands creativity, with chef driven tastings, fashion focused moments, live music and interactive art. Plan to spend time both at the event and around downtown so you can explore local galleries and boutiques while you are here.
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Highlands Motoring Festival
June 11–14, 2026
Four days of scenic drives, social events and a curated car show right in town. Classic and exotic automobiles line up near restaurants and shops, which makes this a perfect weekend for travelers who love both driving and walkable mountain charm.
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Mountaintop Art & Craft Show
June 27–28, 2026
An outdoor showcase for regional artists and makers. Browse booths with fine art, handmade goods and crafts, meet the creators and enjoy live demonstrations, all on a cool Highlands summer style weekend.
More spring happenings
Saturday, March 21 – Spring Exhibition Reception at The Bascom
Free and open to all, this reception is a relaxed way to start a spring visit. Meet artists, explore new exhibitions on The Bascom’s beautiful campus and connect with other art lovers.
Thursday, April 23 – Orchard Sessions at The Farm: Mike Kennebrew
Settle into comfortable seating in the Orchard at Old Edwards’ Farm for an intimate concert from 6 to 8 pm. Enjoy Mike Kennebrew’s folk set with a cash bar and complimentary light bites, with special pricing for Old Edwards Inn and Half Mile Farm hotel guests and members.
Saturday, May 23 – Season Opening Celebration at Highlands Historical Society
Celebrate the start of the season with food, live music and a first look at new exhibits that feature interactive technology. It is an easy addition to a late May weekend in town.
Saturday, May 30 – The Texas Tenors at Highlands Performing Arts
Round out your trip with a high energy performance by The Texas Tenors, blending Broadway, country and classical in an intimate mountain venue.
Choose your weekend now, then book your stay and tickets so you can count down to spring in Highlands with something special on the calendar.