Explore Asheville

An Asheville, North Carolina vacation offers an astonishing variety of activities and attractions—see what The Wall Street Journal has to say about the area. A stay at the Chestnut Street Inn will put you in an ideal location to experience them all! 

From the inn, you can walk to downtown, where you can enjoy shopping, dining, and lots of people watching!

Your Pre-Planned Adventures

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Explore Asheville like a local

Downtown Asheville

A quick ten minute walk gets you to the main drag of Downtown, Broadway Street. When you arrive at the inn we will provide you with a map and show you the best way to walk downtown and some of our favorite spots to check out. The absolute favorites are: The Grove Arcade, Wall Street and its cobblestone sidewalks, the Woolworth Art Walk on Haywood Ave, shopping at East Fork Pottery on Lexington Ave, sipping chocolate at French Broad Chocolate Lounge in Pack Square, Friday night drum circle in Prichard Park and our very own self-guided beer tour in the South Slope.

The Biltmore Estate

One of Asheville’s main attractions, The Biltmore Estate is a must-see for anyone visiting (or living in) Asheville. The 8,000-acre estate features 250 rooms filled with art and antiques, constantly changing exhibits beautiful gardens, 22 miles of hiking trails, a winery, shopping and on-site restaurants. We highly recommend booking tickets in advance and the audio-guide is a must!

biking mountain

Outdoor Adventure

Let us help you get outside! Asheville is one of the most incredible places in the country for outdoor adventure. We can provide you with one of our accessible pre-planned adventures that we base on day-of weather and visibility, or you can come seriously prepared!


Zip Lining– The ultimate place for zip-lining is Navitat. We suggest going for the Blue Ridge Experience. Reservations are required.

Whitewater Rafting– Blue Heron is our go-to for whitewater. Only 30 minutes away from the inn, we love doing their half-day trip and asking if we can go a bit faster and get the big rapids at the end!

Fly Fishing– There are an abundance of amazing spots to hit for our experienced anglers. For those wanting a guide we love our friends at Altamont Anglers.

Mountain Biking- Pisgah Mountain Bike Adventures can help you customize a full or half day bike trip through the Pisgah National Forest.

Hot Air Balloons- Asheville Hot Air Balloons is one of our most trusted balloon guides in Asheville. Sunrise is magical over the mountains!

Hiking– We love using Romantic Asheville as a hiking guide. Their site is full of great recommendations and directions; so helpful when you’re in the mountains with limited GPS!

Below you will find our top three favorite hikes!

Beer City USA

Asheville is a beer-lover’s paradise. With over 50 breweries in town, you couldn’t see them all if you tried! Our guest favorite is Emilie & Arturo’s Self-Guided Walking Beer Tour; 1.2 miles from the inn is our South Slope section of downtown which has about 10 breweries to visit. We tell you where to go and what to eat and drink!

Sierra Nevada is a must see and a wonderful lunch spot to visit after hiking the DuPont Falls. We call it the Biltmore of breweries! The food is incredible and our secret for getting a table fast is to ask where the communal seating is! Looking for a tour? Book in advance!

New Belgium Brewing is located in the Rive Arts District and has a wonderful tour as well. We love skipping over to the Wedge Brewery from there to grab some peanuts and beer and do some people watching!

River Arts District

Nestled in and among old abandoned mills, warehouses and factories is our River Arts District or RAD. The RAD has over 200 Artists in residence with everything from fine art, porcelain pottery, glass, furniture and crafts. You can spend a whole day exploring working studios and galleries! We love to check out the Wedge Studios and then sneak around the back to the Wedge Brewing Company or a beer, walk along Depot Street and our favorite activity is glass blowing at the NC Glass Center. Spots fill up quickly so book in advance! We love All Souls Pizza and White Duck Taco Shop for lunch and Vivian or Bull & Beggar for dinner! The area is also home to New Belgium Brewing!

Funky Antiquing

Asheville is definitely not a “normal” place to do anything, and Antiquing is no exception. One of our favorite things to do on a rainy day is to check out some of Asheville’s quirky antique shops & warehouses. You could spend hours getting lost in the Tobacco Barn, explore antiques and handcrafted items at the strip on Swannanoa River Road, our personal favorite place to find everything from art to motorcycles at the Regeneration Station and browse the incredible collections at Screen Door.

Best Tours

We take our job as Asheville stewards very seriously, but for guests looking for a more structured guide to Asheville, there are many tours that we enjoy!

LaZoom Comedy Bus Tour– by far our favorite way to see Asheville. It’s campy and hilarious and BYOB. You’ll cheeks will hurt from laughing.

Grey Line Trolley Tour– A more classic approach to seeing Asheville. We love that they are hop on/hop off and make stops at the Grove Park Inn and Biltmore Village.

Wild Food Foraging Tours– As Asheville as it gets. Take a “forage to table” tour, get outside and then enjoy a meal.

The Flying Bike Tour– Take an electric bike tour through Asheville. Our guests love this because you see the city and avoid pedaling the hills!

Asheville Food Tours– This is perfect for guests who don’t have enough time to try all of our amazing restaurants! We specifically love Eating Asheville and Asheville Food Tours

The Arts

Asheville has an amazing music and theatre culture that makes us a destination for performing arts in the South. Whether it’s a show at the Diana Wortham Theatre, a tour of the newly renovated Asheville Art Museum, or some live music at the Orange Peel… there’s always something for everyone.

Asheville Art Museum

The Orange Peel

Isis Music Hall

The Grey Eagle

Diana Wortham Theatre

US Cellular Center & Thomas Wolfe Auditorium


North Carolina Arboretum

Only 15 minutes from the inn is the extraordinary NC Arboretum. For guests who don’t have time to visit the Biltmore Estate or for guests looking for the closest hikes to the inn, the Arboretum has it all. The gardens were designed as a research arboretum by Frederick Law Olmsted for George Vanderbilt as part of his Biltmore project. The handicap accessible gardens are extraordinary (we love the bonsai exhibit), and there are also 10 miles of hiking trails. We enjoy hiking along Bent Creek and enjoying the Azalea garden when it’s in bloom. The Arboretum is conveniently located next to a Blue Ridge Parkway entrance.

Farmers Markets

 We LOVE our farmers markets! We are so lucky in WNC to have an abundance of makers and growers. Make sure to check for seasonal hours and openings!

Tuesdays: West Asheville Tailgate Market

Wednesdays: RAD Farmer’s Market

Fridays: East Asheville Tailgate Market

Saturdays: Downtown City Market & North Asheville Tailgate Market (personal favorite)

Fresh market