Your stay in Asheville at the charming Pinecrest Bed & Breakfast promises a perfect mix of history, exploration, and relaxation. Our History Lovers Escape is planned with local partners to make the most of your vacation. Here is an itinerary for 3 nights and 2 days to help you get started.
Arrival & Evening Stroll
Get a head start on your trip when you opt for early check in at 1 pm. Pinecrest offers delights such as hand dipped chocolate strawberries or local cheese board when you need a little tide me over until dinner.
After checking into Pinecrest, take a leisurely stroll through the Montford Historic District, known for its beautifully preserved homes and rich history. Our self guided Montford Walking Tour includes points of interest and otherwise overlooked details.
Enjoy a cozy dinner right in the neighborhood at two award winning restaurants. The ever popular Nine Mile is a perennial winner of Best Overall Restaurant in WNC. Local voters line up for a table at this Caribbean-influenced spot, just one block from the B&B. Or try the Best New Restaurant 2023, Tall John’s, a neighborhood tavern. This historic 1899 building that once housed a church has been carefully restored with original wood frame windows and hardwood floors.
Time your evening right and catch a western sunset……ps, we’ll tell you our favorite spot when you stay at Pinecrest.
Historic Asheville Immersion
Start your morning with a delightful homemade breakfast at Pinecrest and a leisurely morning. Head out toward downtown for a walking tour with Asheville Free Walking Tours. Whether public or private, this engaging tour will guide you through downtown’s historic architecture. See an array of Art Deco gems including the Grove Arcade, Pack Square, and The Basilica of Saint Lawrence, a masterpiece designed by Rafael Guastavino.
Afterward, grab lunch at the Woolworth Walk, home to a fully functional old fashioned Soda Fountain. The space also houses over 170 local artists featuring jewelry, fine art, decorative arts and crafts on two floors.
In the late afternoon, take a scenic ride with Mountaineer Motor Tours in a 1923 Model T, giving you a unique glimpse into Asheville’s past while rolling through its most iconic districts. Tour the Grove Park and Lakeview Park neighborhoods as you explore the history, architecture, and landscape design of the 1920s.
As evening sets in, prepare for a delightful dinner at Luminosa in the historic Flat Iron Hotel where the roaring twenties live again in this recently renovated office building. Savor Italian-inspired cuisine prepared by Chef Graham House in a setting that merges old-world charm with modern elegance. After dinner, see if you can find the speakeasy Red Ribbon Society or opt for a ride in the vintage elevator for a nightcap on the rooftop.
Spend the Day at Historic Biltmore
After another delicious breakfast at Pinecrest, spend your morning exploring the grandeur of Biltmore Estate, the historic home of George Vanderbilt. Stroll through the lavish rooms, stunning gardens and even visit Antler Hill Village for a glimpse into the estate’s agricultural past and America’s most visited winery. Reservations are recommended for lunch on the Estate at The Stable Cafe. Dine on Appalachian comfort food in horse stalls now converted to cozy booths.
Tutankhamun: His Tomb and His Treasures, opens at the estate’s exhibition center on March 21, 2025 and runs until the end of the year. Be transported back to 1922 and archeologist Howard Carter’s fascinating discovery of King Tut’s tomb in a 3-D recreation of the excavation site.
Pinecrest is a lodging partner for Biltmore Estate. Our guests can use a promotion code for savings of $8/ticket or check out our seasonal special offer.
For your last evening, opt for dinner at one of Asheville’s many restaurants. Our curated list of Favorite Restaurants hits just the right notes. Choose from farm-to-table James Beard award winners or go casual at a local brewery. We even know where to get carryout pizza by the slice if you just want to chill on the sunporch.
One More Stop on Departure Day
As your time in Asheville draws to a close, savor your last breakfast at Pinecrest. If time allows, discover Asheville’s creative spirit with a visit to the vibrant art studios of the River Arts District. The north RAD is open after Hurricane Helene. The Folk Art Center, located at MP 382 on the Blue Ridge Parkway, is home to the Southern Highland Craft Guild. Find a memorable souvenir in the Allanstand Craft Shop filled with arts and crafts representing Appalachian artists.
Or learn about Asheville’s most famous author at The Thomas Wolfe Memorial. The author immortalized the boarding house of his youth “My Old Kentucky Home” in his 1929 novel Look Homeward, Angel.
Stay at Pinecrest in Historic Montford
Staying at Pinecrest Bed & Breakfast in Asheville is more than just a place to rest. It’s an experience steeped in charm, comfort, and history. Nestled in the heart of the historic Montford district, this beautifully preserved 1905 home offers a perfect blend of old-world elegance and modern amenities. Inviting common spaces, cozy yet well-appointed rooms, and personalized service makes every stay special. Pinecrest provides a warm and welcoming retreat that truly captures the essence of Asheville.