Spring is trying her best to push away the winter, but during April, we tend to have spring, winter, spring, winter until finally… TaDahhhhh, spring is here. Sometimes that doesn’t happen until mid-May. As a matter of fact, there’s an old-timer’s rule in these mountains: “Don’t plant ANYTHING outside until after Mother’s Day.

Just because spring hasn’t sprung doesn’t mean you can’t plan. There are going to be lots of fun things to do in 2021, and we ALL feel like having a little fun, right?

So, just what IS going on in Highlands? Here are few things to look forward to in May


May 15th- Highlands Rotary presents the Twilight 5K and 10K  Race is on August 15th starting at 6PM at the Kelsey Hutchinson Founders Park. The 5K course is undulating, beginners or walkers will find it friendly, yet the faster runners will be challenged. 10K course is challenging and climbs Bear Pen Mtn.  “Will you eat the Bear or will it eat you”!  Registration and check-in will start at 4PM. Early packet pickup on Friday the night before the race from 4-6 at Highlands Recreation Park. Please allow enough time to get checked in. Parking will be available around the Kelsey Hutchinson Park, Highlands Recreation Park, Highlands Ballfield, and Highlands Post Office. Bring chairs, coolers, refreshments, blankets to join us for the evening music, starting around 7:30PM, it is going to be a blast!!! Glow necklaces for the kids. Rarely above 80 degrees in summer. Always cool in the evening. Get out of the heat! This is your opportunity to come to “cool” Highlands NC and run on the plateau. Kids under 5 run 5K for free. Kids 5 to 9 $10.00 for 5K. Must be 15 years of age or over to run 10K, parts of the course will be unmonitored and open to car traffic.  Day of race price will be $40.00 for 5K and $50.00 for 10K, so sign up early.  Here’s the link for more info: https://www.highlandstwilight5kand10k.com/ 


May 21st- The first of the season Friday Night Live performance, with music provided by Silly Ridge Roundup. These events are FREE and are on Main Street in the courtyard where Wild Thyme Restaurant, Colonel Mustard, T.J. Bailey’s, Silver Eagle, and of course, you can’t have all that lively music without ice cream from Kilwin’s! (well, you could, but it may not be as much fun)

Town Square, Highlands

6:00 p.m. – 8:00 p.m.

Silly Ridge RoundUp is a Highlands-based troupe that offers an eclectic blend of Americana, bluegrass, folk music, and brings fun, energy, and toe-tapping music to any event throughout the Highlands – Cashiers plateau. Although the band is built around the three core members of David Goodrow, ( lead vocals, guitar, percussion), Knight Martorell, ( banjo, fiddle, harmonica, harmony vocals), and Carter Geigerich, (mandolin, dobro, vocals ), they often expand, drawing upon a broad circle of professional-level, good friends.  Silly Ridge RoundUp is a strong dose of musical fun, without the hangover.


May 22nd – Meander in May – Meander our vibrant downtown where refined taste is packaged in a small-town atmosphere. Enjoy live performances, artisans, craftsmen, and demonstrations courtesy of Visit Highlands, NC and Highlands Chamber of Commerce while restaurants and shops keep you fueled for exploration.
This free, self-guided event on Saturday, May 22nd is from 11am – 4pm with the final concert at 6pm in Kelsey Hutchinson Park. Music provided by The Caribbean Boys.  Masks and social distancing will be required. Highlands is serious about our Arts; you do not want to miss this immersive and interactive arts experience in downtown Highlands, NC!

May 28th-Friday Night Live Concert – Trudition

  • Presented By: Highlands Chamber of Commerce
  • Dates: May 28, 2021
  • Address: 108 Main Street,
  • Time: 6:00 PM to 8:00 PM

May 29th – The Annual Mountain Garden Club Plant Sale– This event tends to sell out quickly, so come early. No early birds. Sale is 9:00 am to Noon. These plants are local to the Highlands area and have been lovingly dug and potted by Mountain Garden Club members. The proceeds to renewable scholarships for Highlands School students furthering their education in environmental, horticultural, and other studies, as well as beautification projects by the club. Here’s the link to know more about this outstanding civic organization. https://www.highlandsmountaingardenclub.org/ 


May 29th -Saturdays on Pine – Ashley Heath & Her Heathens

  • Presented By: Highlands Chamber of Commerce
  • Dates: May 29, 2021
  • Location: Kelsey Hutchinson Park, Highlands
  • Address: Pine Street, Highlands, NC 2874
  • Time: 6:00 PM to 8:00 PM
  • Price: FREE

Of course, any time of year, you can visit the area’s waterfalls, hike some amazing trails, shop, in some of the most eclectic shops in the region, dine in some of the BEST restaurants in the region, too. Don’t take our word for it, come and see for yourself.



One of Highlands’ favorites is the Highlands Nature Center and Biological Station. There are a few picnic tables dispersed around the grounds so you can enjoy nature’s display. Although the nature trails and Botanical Gardens are open year-round, they also offer summer camps, programs and other things. Here’s the link so you can see what’s going on and know when you can go. https://highlandsbiological.org/botanical-garden/

Here are few more links of things to do in the area: (Please tell them you heard about them from Chambers Realty)

Highlands Excursions. We see these people EVERYWHERE. Here’s a link to find out more and how to arrange for your trip. https://www.overlandunlimited.com/

Zipline Fun – Several tours to choose from and a giant mountain swing, hiking and guided trails. Here’s the link to find out more: https://www.highlandsaerialpark.com/?utm_source=GMBlisting&utm_medium=organic

If you want to go on a hike in the woods, but don’t have a lot of time, try some of the Greenway Trails. Some of these are very close to Main Street, which makes it easy for part of a family to shop while the rest take a hike. You will be IN the woods, but not secluded.  Here’s a link to find out more about the Highlands Greenway Trails. https://www.americantrails.org/resources/highlands-plateau-greenway-highlands-north-carolina

Phew! Now, I’m tired, and you will be too. There’s only one thing left to do- find a great rental to rest your weary bones. Come and stay a weekend, a week or a month in Highlands. This post just touches the surface!

There’s always something going on in Highlands, NC!