On the way to Highlands, you’ll follow winding mountain roads with forest, rock cuts, wide views, and even waterfalls along the way. No matter which direction you come from, the drive sets the tone before you reach town.
Highlands brings together mountain ease, thoughtful dining, independent shops, art, music, and quick access to the outdoors. You might begin the day on a trail, stop by a waterfall, spend the afternoon downtown, then end over dinner just a few blocks away.
For a first visit, the best way to get to know Highlands is to enjoy both sides of it: the natural beauty around town and the local life at its center.
Start With Local Music
If your visit includes a Wednesday evening, Bluegrass Night at The Ugly Dog Pub is a natural place to begin. It is casual, lively, and a favorite evening stop in town.
Bluegrass has long been part of mountain life, and hearing it in Highlands gives you a relaxed way into the local music scene. Pull up a seat, order dinner or a drink, and enjoy the evening.
Before you go: Confirm the current music schedule with The Ugly Dog Pub before planning your evening.
Take Your Time Downtown
Main Street gives you a clear feel for Highlands, but some of the best stops are just off the main stretch. Give yourself time to wander Main Street, North Fourth Street, South Fourth Street, and the side streets around downtown.
For home goods and interiors, Dutchmans carries furniture, bedding, drapery design, and home pieces with a collected mountain feel. Just off Main Street, ACP Home Interiors is another worthwhile stop for furniture, decor, accessories, and pieces that bring Highlands style home with you.
For clothing and outdoor gear, Highland Hiker is a trusted stop for hikers, fishermen, and travelers. Bear Mountain Outfitters is another strong option for footwear, clothing, and practical pieces for a Highlands weekend.
If you are looking for something to wear into the evening, Highlands Hatter on North Fourth Street offers custom hats, private fittings, and finishing details. Nearby, Allison Diane Clothing, Elevation of Highlands, and TJ Bailey’s are easy additions if you want clothing, accessories, or a more polished mountain look.
For gifts, jewelry, art, and antiques, make time for a slower browse. Silver Eagle Gallery carries crystals, rocks, jewelry, knives, and gifts. Highlands Fine Art and Estate Jewelry and Mirror Lake Antiques are good stops for pieces with a little more history and staying power.
If you are traveling with kids or pets, downtown has practical stops for them too. Highlands Kids on North Fourth Street is an easy stop before dinner or music, while Highlands Mountain Paws carries treats, toys, apparel, grooming products, and gifts for dogs and dog lovers.
For a break from shopping, Highlands Wine Shoppe has wine, outdoor seating, and a front-row view of downtown. If you want a practical stop before the evening, Whole Life Market on North Fourth Street is useful for snacks, natural products, gifts, and a juice from Nectar Juice Bar.
Before you go: Check shop hours before building your day around a specific stop, especially on Sundays, holidays, and busy event weekends.
Spend Time Outside
A first visit to Highlands should leave room for the outdoors, whether you want an easy walk, a mountain overlook, or time near a waterfall.
The Highlands Nature Center and nearby garden trails are a good place to start. They give you a close look at the plants, wildlife, and natural beauty of the Highlands Plateau, especially if you like to learn as you explore.
Across from the Nature Center area, Sunset Rock is one of the best short walks near town. The trail is considered easy, with about a half-mile walk to the top. From there, you can see downtown Highlands and Brushy Face Mountain. Park with care and do not block the private drive.
For a wider mountain view, Whiteside Mountain is a Highlands favorite. The moderate two-mile loop has panoramic views and dramatic cliffs, with a fee parking area near the trailhead.
Glen Falls is a good choice if you want a waterfall hike with a little more effort. The route drops on the way in, so the way back takes more effort. Wear proper shoes, bring water, and give yourself plenty of time.
See the Waterfalls with Care
Bridal Veil Falls and Dry Falls are two classic waterfall stops near Highlands.
Bridal Veil Falls is close to town and easy to view from U.S. 64 West. Dry Falls is one of the area’s best-known waterfall stops, with a path that leads behind the falls and an accessible viewing platform.
Important waterfall note: Dry Falls parking is limited. If the lot is full, return later. Do not block the road or park along the roadside. Keeping the road clear protects visitors, residents, and emergency access.
Enjoy Highlands’ waterfalls safely by staying on marked trails, following posted signs, keeping children and pets close, and never climbing on or around waterfalls.
Visit The Bascom
The Bascom is worth a stop if you want to see the creative side of Highlands. Located on a former horse farm near downtown, The Bascom has exhibitions, classes, workshops, retail, outdoor spaces, sculpture, trails, and mountain views.
It is more than a gallery visit. The Bascom gives you a look at how art, education, and community shape life in Highlands.
Plan for an Evening Out
If you are visiting during the weekend, check the local event calendar for concerts and seasonal gatherings, including the Outdoor Concert Series when in season. Free outdoor music is a simple way to spend the evening with locals and other visitors. Bring a chair and find a spot.
Before you go: Confirm current dates, times, and seasonality before making plans.
End With a Good Meal
Food is a big part of Highlands. For a first trip, let the day guide the table: Highlands Smokehouse for casual barbecue after a waterfall outing, Wild Thyme for a cozy dinner, Four65 for wood-fired pizza after a Main Street walk, Stubborn Buddha for Thai flavors, or Highlands Tavern for dinner in the middle of town.
*Check hours and reservations before you go, especially during weekends and peak seasons.*
Your First Highlands Visit
Highlands is best enjoyed without packing the schedule too tightly. A good weekend might include a morning trail, a glass of wine on Main Street, an evening concert, and a waterfall stop before heading back to town.
Save this as a starting point for your first weekend in Highlands.