Sips & Sights: A High Point Fall Crawl

July 11, 2025
By: Haley Overturf

Fall in High Point isn’t just pumpkin patches—it’s cider in hand, crisp air on your cheeks, and live music echoing through downtown. We’ve crafted three self-guided “crawls” to help you enjoy the best of autumn one sip, step, and bite at a time. Here is your guide to three different sip-and-stroll style experiences. 

1. Fall Flavors Crawl

Start crisp fall mornings or wind down with cozy afternoon indulgences at these local gems that capture fall’s most nostalgic flavors.

Coffee Crawl

  • DeBeen Espresso: It doesn’t get much cozier than DeBeen! This High Point staple is known for its fan-favorite fall flavors, including the maple cinnamon latte and the beloved pumpkin chai-coffski, a blend of espresso and warm chai spices with a hint of pumpkin!

    Insider tip    : Grab your sweet pick-me-up before or after a rejuvenating yoga class at Pure Light Yoga right next door!
  • Lil’s Coffee Bar: Lil’s is the place to be on a crisp fall day in High Point. Settle in with a hot latte, tea, or cider while enjoying downtown views. Stay on the lookout for this year’s menu, but last year’s featured delicious options like a pumpkin pie latte, salted caramel cold brew, and apple cider tea.

  • A Special Blend: If you enjoy your fall flavors with a side of making a difference, A Special Blend will be your go-to. This coffee shop employs individuals with intellectual and developmental disabilities who can’t wait to craft your perfect fall treat!

  • Joy Bar Coffee Co.: With two convenient locations, you’re never far from your favorite fall drink. Joy Bar Coffee Co. prides itself on its creative takes on fall flavors.

    Insider tip: The pumpkin saffron latte at Joy Bar is an absolute must-try. This unique take on the PSL is sure to warm you right up!

View a full list of coffee shops here.
 

Sweets & Treats Trail

The best part about High Point bakeries? Many of them are serving up delicious coffees and espresso drinks to pair with those sweets & treats!

  • Dot and Pearl’s Bakery: Located inside The Market, Dot & Pearl’s Bakery has all the seasonal flavors you’re looking for. Whether it’s cake, pie, cookies, or coffee you’re craving, their menu is sure to satisfy. Plus you get to shop for gifts, home decor, and more while you’re at it!

  • Sweet Dough Bake Shop: Sweet Dough knows how to do fall flavors! Indulge in pumpkin cream cheese muffins, apple-filled cruffins (I bet you didn’t know you need a croissant-muffin combo!), pumpkin chocolate chip cake slices, and more!

  • Cara’s Cookie Company: Conveniently located in Stock + Grain, High Point’s food hall, Cara’s Cookie Company is serving up the essential sweet treat and coffee combo. Be sure to stop in and see what fall flavors they’ll be baking up this year!

  • Duck Donuts: Pumpkin streusel and caramel apple pie and maple bacon, oh my! Can’t pick? Might as well get the fall assortment and try them all. Duck Donuts is an NC-favorite and a must-try when in High Point. 

View a full list of bakeries here.

2. Beer, Wine, and Spirits Crawl

Whether you’re in the mood for a crisp cider, a seasonal ale, or something stronger, High Point’s beverage scene is pouring fall by the glassful.

Your Beverage Trail

  • Brown Truck Brewery: Enjoy rotating seasonal brews on their leafy patio. Watch for Oktoberfest specials or amber ales.

  • Goofy Foot Taproom: A hidden gem with a community vibe and frequent food truck partners—perfect for casual sips and bites.

  • Nomad Wine Works: Try their small-batch wines and ciders—often with fun, seasonal flights available.

  • Founding Fathers Distillery: For a warm-up with a kick, sample bourbon, moonshine, or cinnamon whiskey crafted right here in High Point.

    Insider tip: Many of these spots feature trivia nights, live music, or fall-themed events on weekends—check their socials for the latest.

3. Fall Foliage Crawl

There’s no better way to experience fall’s changing colors than by walking right through them. Grab your latte to-go and hit the trails.

Leaf-Lover’s Stops

  • High Point City Lake Park: Scenic water backdrops, a pedestrian bridge across the water, wooded paths, and wide-open picnic areas make this the perfect spot for leaf peeping. Fall in High Point is also mild, so you can still enjoy kayak, canoe, and stand up paddleboard rentals through September!

  • Oak Hollow Park: Experience the beauty of fall against the backdrop of Oak Hollow Lake. There’s even a dock for the perfect fall picnic, walking trails, and kayak, paddleboard, and sailboat rentals.

  • Greenway Trails: Walk, run, or bike through vibrant canopies connecting neighborhoods and nature.

    Insider tip: Download the Piedmont Discovery app before you visit to explore all area parks. This free app allows you to view trails by level of difficulty and terrain, get directions, and find park amenities.

Bonus: Can't-Miss Fall Events

Make it a full-day or weekend adventure by pairing your crawl with one of these upcoming events. Whether you want to dance, dine, or discover something new, High Point has something brewing.