When autumn paints the Ozarks in warm hues of orange and gold, there’s no better time to hit the road for a nostalgic journey. This fall-themed itinerary follows Highway 165 and nearby byways through Branson, Hollister, Branson West, Kimberling City, and Ridgedale—connecting scenic overlooks, retro diners, quirky shops, and photo-worthy Americana delights. Embrace crisp air, lake vistas, and small-town charm that make you feel like you’ve stepped back into the “good ol’ days.”
Branson: Scenic Views & Classic Downtown Charms
Highway 165 Scenic Overlook
Start at the famous overlook just a few miles from Branson’s entertainment district. From the ridgetops you’ll catch sweeping views of Table Rock Lake and the rolling Ozark hills in full fall color. Sunrise and sunset are magic hours—golden light, cool temps, and plenty of space for family photos. A cozy coffee stop across the street makes it easy to sip a latte or hot cocoa while you soak in the view. (Travel tip: little ones should stay inside the fencing along the bluff.)
Historic Downtown & Dick’s 5 & 10
Head into Downtown Branson for a dose of small-town nostalgia. Stroll Main Street to Dick’s 5 & 10, an old-school variety store packed with retro toys, classic candy, puzzles, and Ozarks curios. It’s part store, part mini-museum, and 100% time capsule—kids hunt for trinkets while grandparents point out memories from decades past. Slow down, wander the aisles, and let serendipity do its thing.
Classic Eateries
Bring your appetite. Branson Café (est. 1910) dishes up diner staples and legendary pies—the kind of place where a plate of biscuits and gravy tastes like Saturday morning at Grandma’s. Craving a burger-and-malt moment? Billy Bob’s Dairyland keeps things delightfully simple with griddle-smashed patties, thick shakes, and retro vibes. However you lunch, you’ll feel plugged into Branson’s living history.
Hollister: English Village Whimsy & Fall Festivals
Just across Lake Taneycomo, Hollister charms with Downing Street’s Tudor-style storefronts and old-world look. Pop into boutiques and cafés, admire the stone-and-timber architecture, and snag a porch-side treat.
If you’re visiting in early October, plan for Hollister’s Grape & Fall Festival—a community celebration with craft vendors, live entertainment, food booths, and a crowd-pleasing grape stomp. It’s small-town fun at its best and an easy way to mingle with locals. Between shops, grab a latte or spiced cider at Vintage Paris Coffee & Wine—an artsy, welcoming spot perfect for a quick recharge.
Branson West: Pioneers, Caverns & Ozark Craft
Rolling west on Highway 76, you’ll reach Branson West, gateway to Ozark countryside and classic attractions.
Silver Dollar City (Optional Full-Day Detour)
If your crew can spare a day, the park’s Harvest Festival blends fall food, artisan demos, and a glowing “Pumpkins in the City” after dusk. By day, watch glassblowers and pumpkin carvers at work; by night, stroll past thousands of illuminated gourds and larger-than-life pumpkin sculptures. It’s wholesome, imaginative, and perfect for multi-generational memories.
Prefer something quicker? Take a guided tour of this historic cave, nicknamed “Fairy Cave.” Kids love the winding stairs and otherworldly formations; above ground you’ll find mini-golf and nature trails—classic Ozarks roadside fun with a nature-first twist.
Shepherd of the Hills Farm & Inspiration Tower
On the west edge of Branson, step into Ozarks lore at the homestead that inspired the 1907 novel The Shepherd of the Hills. Tour the preserved cabin and church, then ride the elevator to the 230-foot Inspiration Tower for a 360° panorama—a patchwork of reds, oranges, and golds stretching across the hills. (Seasonally, the property also hosts a kid-friendly pumpkin fest—great to pair with the tower view.)
Fuel Stop: Billy Gail’s Café
Housed in a rustic log cabin, Billy Gail’s is famous for hubcap-sized pancakes, pumpkin-spice specials, and country-breakfast plates. Vintage license plates and farm tools on the walls set the “backroads general store” mood. Come hungry; leave happy.
Kimberling City: Lakeside Views & Homecooked Goodness
Head southwest to Kimberling City, where the bridge arches across Table Rock Lake—a perfect quick stop for photos of crimson hills reflecting on blue water. Life moves slower here: houseboats bob in quiet coves, fishermen drift along the shoreline, and fall colors wrap the hills like a quilt.
For a hearty, hometown meal, slide into a booth at Ma’s Place on Highway 13. This cozy diner serves breakfast all day, smoked BBQ, and comfort-food classics. Regulars rave about biscuits & gravy, fried chicken, and pie—served with a side of friendly Ozarks chatter. It’s budget-friendly, family-friendly, and exactly the kind of spot that makes road trips memorable.
Before rolling on, stock up on snacks at a local market or take a brief detour to a lakeside overlook. On clear afternoons, you can sometimes catch fiery foliage mirrored on the water—peak mid-October is the sweet spot.
Ridgedale: Sunset on the Ridge
Loop southeast toward Ridgedale for big-sky views and one last golden-hour moment. At Top of the Rock, stroll the grounds for sweeping overlooks of forested hills and the blue expanse of Table Rock Lake. If time allows, the Lost Canyon Cave Trail (via golf cart) winds past waterfalls, bluffs, and a surprise underground cascade—kids love the sense of discovery.
As the day fades, gather along the railing for the sunset ceremony: an old Scottish bagpiper plays while the sky turns pink and purple. A historic cannon booms to mark day’s end, and guests offer a simple toast to the view. It’s a goosebumps-worthy finale to your fall drive.
Bring It Home to The Ozarker
End your day the Ozarks way: pile into the car with pumpkin donuts and pie slices for later, then settle in at The Ozarker Lodge for a campfire night by the creek. Swap stories, make s’mores, and listen to the water as the stars come out. Tomorrow can be more leaf-peeping, more diner stops, more “one quick photo” turnouts. But for tonight, breathe deep and enjoy the glow. From scenic highways and lake views to old-time diners and delightful small towns, this Highway 165 loop is filled with the kind of moments that become family legends. As we like to say around here: These are the good ol’ days. Enjoy every mile, every bite, and every memory made along the way.