A Four-Day Escape at Graylyn Estate: Wine, Walks, and Winston-Salem Charm

Graylyn Estate doesn’t ease you in gently—it sweeps you in. We arrived late at night to find the main house lit up like a castle, glowing against the dark like it had been waiting for us. It felt dramatic, cinematic, and entirely unexpected for a Wednesday-night arrival.

We stayed in The Mews (see video below), a tucked-away section of the estate just a short drive or 10-minute walk from the main house. The Mews has its own personality—quiet courtyards, old-world charm, and the comforting sense of being slightly removed from everything while still fully part of the Graylyn experience.

DAY 1: Settling In + Letting Graylyn Estate Do Its Work

Morning at Graylyn feels different. Soft, unhurried, restorative. Breakfast unfolds slowly. The grounds invite wandering. The hallways pull you in with portraits and quiet corners.

There’s no agenda on Day 1—just space. Space to settle. Space to breathe. Space to let your shoulders drop.

DAY 2: JOLO Winery — JW, Perfect Pairings, and the Lunch That Won the Weekend

JOLO Winery anchored Day 2, and it’s easy to see why people build entire weekends around it.

JW: The Person Who Makes JOLO Unforgettable

Our tasting host, JW, guided us through JOLO’s wines with a mix of humor, storytelling, and real expertise. He made the experience personal—not a script, not a speech, but a conversation.

You don’t forget hosts like that.

Lunch Worth Talking About

Lunch was hosted in a beautiful dining room and was delish. The butternut squash ravioli was the standout—rich, balanced, and the kind of dish that makes you want to come back. 

We Left as Members (and With Bottles)

We signed up for the wine membership and left with multiple bottles because the experience was that good. JOLO didn’t just impress us—it won us over.

Quiet Night at Graylyn

We ended the day quietly in The Mews—wandering the grounds, reading, unwinding.

DAY 3: Art + Trolley Tour + Old Salem + EasyTalk + Dinner at Mozelle’s

Day 3 had layers: history, creativity, connection, and comfort food.

Sawtooth School for Visual Art: Creativity With Its Sleeves Rolled Up

Before we hopped on the trolley, we spent the morning at Sawtooth School for Visual Art—a place that feels less like an art school and more like a living workshop of ideas.

Sawtooth has been part of Winston-Salem’s creative DNA for decades, and you feel that legacy the minute you walk in. Studios hum with activity—glass fusing, ceramics, woodworking, metals, drawing, textiles. It’s hands-on, grounded, and refreshingly unpretentious.

What stood out most:

People weren’t just making things. They were fully immersed.

The kind of focus that’s rare these days—the kind that makes you want to sit down at a wheel or torch or table and learn something new just because you can.

There’s something deeply inspiring about spaces where creativity isn’t displayed behind glass but happening right in front of you. Sawtooth brings that energy beautifully. It was the perfect prelude to a day spent learning Winston-Salem’s story.

Winston-Salem Trolley Tour: A Moving Story of the City

The trolley tour with Triad Eco Adventures wasn’t just a ride through town—it was a narrative. Mark was our guide, and his enthusiasm for the city was contagious! We traced Winston-Salem’s past and present through:

• sweeping historic neighborhoods

• revitalized industrial districts

• pockets of modern innovation

• architectural gems with long family stories

It gave the city depth. It gave us context. It made Winston-Salem feel alive in a way you only understand when someone who knows the city shares it with you.

Old Salem: A Walk Into Another Time

Old Salem is immersive in the calmest way possible—gardens, timbered buildings, bakers working over open hearths, craftspeople demonstrating traditional skills. It feels preserved, but not frozen. Historic, but not staged. It’s thoughtful, quiet, and surprisingly moving.

EasyTalk: The Speakeasy You Immediately Want to Return To

Before dinner, we stepped into EasyTalk and discovered one of Winston-Salem’s treasures.

David, the owner, is the reason the space works. Warm. Intuitive. Grounded. He curates the experience without ever making it feel curated.

The Cocktail Games

We played:

• Roll the Dice → get a flavor profile

• Guess the Cocktail → decode David’s creation

It was interactive, smart, and just plain fun. We stayed longer than planned because the vibe was magnetic.

Dinner at Mozelle’s

Dinner at Mozelle’s was the perfect finish.

Our server, Lexi, was outstanding—warm, attentive, intuitive. The kind of server who elevates an already great meal.

The food delivered:

• Shrimp & Grits — creamy, deeply flavorful

• Tomato Pie — their signature dish, absolutely worth the hype

• Coconut Pie to-go — eaten later at Graylyn… delish

Mozelle’s is a staple for a reason.

DAY 4: Reynolda — Art, Architecture, Reinvention, and a Final Deep Breath

We saved Reynolda for the final day, and it proved to be the perfect closing chapter — reflective, inspiring, and unexpectedly revealing about Winston-Salem’s spirit of reinvention.

Reynolda Museum: A Home Turned Into a Cultural Landscape

Reynolda began as the 1917 country estate of Katharine and R.J. Reynolds — a model tobacco-era estate built with intention: light, intellectual curiosity, and community. What’s remarkable is how that legacy was repurposed. Instead of becoming another historic site frozen in time, Reynolda has evolved into a living cultural space that blends art, architecture, history, and education seamlessly.

Walking through the museum feels like stepping into a timeline where the past and present coexist comfortably. The art is thoughtfully curated — American art, Southern stories, contemporary perspectives — all woven into a space that still feels like a home.

Nothing feels static.

Everything feels cared for.

Reynolda is preservation with purpose.

Reynolda Gardens: Nature Designed for Reflection, Not Spectacle

The gardens and grounds stretch across 130 acres, but nothing about them feels sprawling in an overwhelming way. Instead, they unfold gently:

• greenhouses repurposed for community and education

• walking paths that wind through trees and historic structures

• formal gardens that still hold their original design integrity

Reynolda Village: A Brilliant Example of Adaptive Reuse

One of the most inspiring aspects of Reynolda is the Village, which sits on the original estate land. What was once the support area for the estate — barns, staff housing, workshops, and dairy buildings — was later converted into a carefully considered commercial village.

And here’s where the innovation shines.

Instead of letting the “mall era” swallow the space in the typical 1980s strip-mall way, Reynolda Village was designed as a human-scale, community-centered hub:

• boutiques inside old barns

• coffee shops tucked into former farm buildings

• restaurants living in converted cottages

• studios and shops woven through walkable paths

It’s adaptive reuse done right — thoughtful, respectful of the past, but forward-looking in how people gather and experience space today.

It’s also a subtle lesson: Winston-Salem reinvented a former estate economy and a former “mall” concept into something that feels like a living, breathing neighborhood. No big-box mentality. No parking-lot sprawl. Just intentional design and a sense of preservation-meets-progress.

Walking through Reynolda Village feels like stepping into a quiet manifesto about how places can evolve without losing themselves.

Reynolda as a Mirror for Winston-Salem’s Larger Story

This was where the entire trip clicked into place.

Reynolda — with its museum, gardens, village, and adaptive reuse — is a perfect reflection of what Winston-Salem is doing citywide:

• honoring history without clinging to it

• repurposing rather than replacing

• innovating in ways that feel grounded, not flashy

• blending creativity with community

It’s a city that reinvents thoughtfully.

A city where old tobacco warehouses become innovation hubs.

Where historic homes become museums.

Where former estate buildings become shops and cafés.

Where preservation doesn’t mean stagnation — it means reinvention.

Standing in Reynolda, it becomes clear that Winston-Salem isn’t just charming.

It’s intellectually charming.

Quietly progressive.

Rooted and imaginative at the same time.

A Note on the Purpose of Trips

Some trips are about mixing work and relaxation. Others are for regrouping, resetting, or getting inspiration in a way you can’t plan for.

This trip fell into that second category.

By plugging into this experience—Graylyn’s calm, JOLO’s hospitality, Old Salem’s history, EasyTalk’s creativity, Mozelle’s warmth, and Reynolda’s beauty—I found myself learning, absorbing, and feeling genuinely inspired by the innovation happening in Winston-Salem.

It reminded me that travel isn’t always about escape. Sometimes it’s about encountering a place that expands your thinking.

Winston-Salem did that.

Why This Trip Works

• Graylyn feels cinematic at night + restorative in the morning

• The Mews offers privacy and charm

• JOLO, especially with JW, is exceptional

• The trolley tour gives context and meaning

• Old Salem adds depth and presence

• EasyTalk is connection, creativity, and surprise

• Mozelle’s (and Lexi!) anchors the culinary experience

• Reynolda provides art, calm, and perspective

• And Winston-Salem quietly reveals itself as a city full of innovation

  
  

It’s a rare mix—and an easy one to fall in love with.