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We're looking forward to celebrating with you in Summer 2026
We're looking forward to celebrating with you in Summer 2026

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    Things To Do

Things To Do

While visiting Downtown Winston we wanted to share a few of our favorite places. If you're looking for something specific please reach out. This is my favorite part - connecting you to this city that I have loved and has loved me back. We hope you get to enjoy a little piece while you're here.

Bobby Boy Bakeshop

845 South Poplar Street, Winston-Salem, NC 27101

An all time favorite Saturday morning pastry stop. We planned part of the wedding here. Located in the Buena Vista neighborhood of Winston-Salem and a new location on Poplar, they’re an artisanal bakeshop committed to using the highest quality ingredients in our pastries, coffees, and breads.

Cobblestone Farmers Market

1007 Marshall Street Southwest, Winston-Salem, NC 27101

Saturday AM farmers market. A treat for sure - stop here before or after you head to Bobby Boy about a 1/2 block away.

Krankies

211 3rd Street East, Winston-Salem, NC 27101

Brunch spot. Julien wouldn't be who she is without the friends she met at this space - former music venue...art hotel...long time coffee roaster and biscuit maker!

Brothers Pizzeria

214 West 4th Street, Winston-Salem, NC 27101

Late night pizza downtown - closer to the hotels than Burke St...a little on the wild side. Love the garlic knots.

Burke Street Pizza Burke St.

1140 Burke Street, Winston-Salem, NC 27101

Late night pizza downtown. Perfect. Love the wings too.

Yamas Mediterranean Street Food

624 West 4th Street, Winston-Salem, NC 27101

Healthy easy option downtown. Easy salads and bowls - Mediterranean style. We love to take Jack here during the week for a quick dinner out of the house.

Fair Witness Fancy Drinks

290 4th Street East, Winston-Salem, NC 27101

Fun Cocktail Bar - not a dive bar but not high end - very casual.

Kaleideum

120 West 3rd Street, Winston-Salem, NC 27101

Have kids? Go here. So fun - multi layer play house. Julien's non-profit, Twin City Santa, started having their yearly holiday toy drive here last year and it's great for adults and kids a like.

The Quarry at Grant Park

1790 Quarry Rd, Winston-Salem, NC 27107

Have kids? Go here for the playground! Close enough to downtown, free parking and nice facilities. HUGE play ground and a fun overlook around the rock quarry. You may even spot freshwater jellyfish! These natural phenomena have been noted there for years, adding to the unique ecosystem of the area that is being developed into Quarry Park

Little Pep - Cutest Damn Wine Bar

533 Trade Street Northwest, Winston-Salem, NC 27101

Ah - right in the heart of downtown arts district. Cute, fun, great owners. Fun fact - this used to be an empty brick hole in the wall with no bathroom and particleboard as floors with graffiti everywhere - I grew up seeing bands here.

Downtown Breweries

There's a few - you'll try Foothills on Saturday night. (the oldest) We love Tropical Shirts and the Irish Stout at Wiseman. If we go to one this is our go to. Fiddlin' Fish and maybe Radar Brewing is still around. We have two distilleries downtown - Broad Branch and Sutlers - we're partial to Sutlers but it's not always open to the public.

Old Salem Museums & Gardens

900 Old Salem Road, Winston-Salem, NC 27101

Like history? Go here: Old Salem Museums & Gardens is a historic site telling the stories of people, including Moravian, Black, and Indigenous peoples, in the American South. In addition to having two National Historic Landmark buildings, the Salem Tavern and the Single Brother’s House, Old Salem was designated as a National Historic Landmark (NHL) District in 1966.

Parks and Gardens

Reynolda Gardens is beautiful with lots of flowers and walking paths - about 2 miles from downtown, has a magnificent art gallery and May Way dumplings (recommend). Bailey Park - downtown grassy area usually some music going on (close to Fair Witness and Krankies Coffee). Salem Lake (semi close, walk a path around it, canoe), Pilot Mountain - about 35 minutes away and an easy hike, Hanging Rock - swimming lake, semi tough hikes about 45 minutes away.

Acadia Foods

228 West Acadia Avenue, Winston-Salem, NC 27127

Owned by our dear friend Jessica McClure. One of you will sit at Jessica's cake table. Do you love collard greens? This is the spot for the best collard melt you've ever had (bacon or no bacon). Lots of vegan and vegetarian items! About 3.5 miles from downtown.

Slappy's Chicken

200 West Acadia Avenue, Winston-Salem, NC 27127

Hot chicken and sides in the south side of Winston-Salem, North Carolina. This is one of Rob's favorites. About 3.5 miles from downtown.

For all the days along the way
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