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Hilltop Hikes to Rooftop Bars: Plan the Ultimate Missouri Pivot

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Castlewood State Park
Jack Stack Barbecue
Ha Ha Tonka State Park
Rock Bridge Memorial State
The Garrison
Top of the Rock at Big Cedar Lodge

Pack your hiking boots and your high heels for a Missouri adventure that promises grit and glitter. From rugged hilltop hikes to upscale restaurants and rooftop bars, experience the best of both worlds in the Show-Me State. Gather a group of friends for a getaway to explore the outdoors, sample local cuisine, and end the day with a celebratory toast.

A woman admires the view of Meramec River at Castlewood State Park.
Catch a view of the Meramec River on a hike at Castlewood State Park near St. Louis.

St. Louis

Hike:  An extensive trail system at Castlewood State Park travels through meadows and forests to the top of steep limestone bluffs. Discover breathtaking views of the Meramec River on the Lone Wolf Trail. The park is also a popular spot for mountain biking, fishing and canoeing.

Dine: Head to The Hill neighborhood for authentic Italian specialties at Charlie Gitto’s on the Hill or Mamma’s on The Hill. Don’t miss the toasted ravioli – it was invented in St. Louis.

Celebrate: Top off the evening at the Chase Park Plaza with a drink at the poolside bar on the third floor. The hotel is located in the city’s bustling Central West End district.     

Kansas City

Hike: Escape to the outdoors at the Burr Oak Woods Conservation Nature Center, just minutes from downtown Kansas City. Bethany Falls Trail, one of six trails at the nature center, travels through restored woodlands, a savannah and rock outcroppings.

Dine: Savor some of Kansas City’s world-famous barbecue at the iconic Country Club Plaza. Find a variety of hickory-smoked meats, from burnt ends (a Kansas City tradition) to lamb ribs, at Jack Stack Barbecue – Country Club Plaza. Or choose from a selection of entrees – including sushi or a succulent steak, at Gram & Dun.

Celebrate: Panoramic views of Kansas City provide the perfect backdrop for a creative cocktail or craft beer at the Percheron Rooftop Bar. Located in the Crossroads Hotel, the bar is a popular gathering spot in the city’s vibrant Crossroads Art District.

Craft cocktails sit on a table with the Kansas City skyline in the background at Percheron Rooftop Bar.
Choose from a variety of handcrafted cocktails at the Percheron Rooftop Bar in Kansas City.

Lake of the Ozarks

Hike: More than 15 miles of winding trails await at Ha Ha Tonka State Park. The Collosseum Trail takes you beneath a natural bridge, through a sink hole and up a steep incline to reach the remains of a 1905 European-style rock “castle.” Follow the Spring Trail to Missouri’s 12th largest spring, pumping 58 million gallons of water a day into the Lake of the Ozarks.

Dine: Linger over dinner and a Lake of the Ozarks sunset view at JB Hooks. The expansive menu includes steaks, chicken and seafood.

Celebrate: Sip a signature cocktail and admire views of the lake in the Sky Bar at The Encore Lakeside Grill. The entertainment complex features multiple entertainment stages and two pools – an adults-only pool and a pool with a swim-up bar.

See the ruins of a European-style “castle,” a natural bridge and a freshwater spring at Ha Ha Tonka State Park near Lake of the Ozarks.

Central Missouri

Hike: More than 27 miles of trails crisscross Rock Bridge Memorial State Park, 5 miles south of Columbia. A boardwalk takes you through a double sinkhole to an underground stream at Devil’s Icebox.

Dine: CC’s City Broiler pairs fine dining with a relaxed atmosphere in Columbia. The menu offers an array of steaks, seafood and an extensive wine list.

Celebrate: Enjoy the view and the wine at a “rooftop bar” designed by Mother Nature. Perched on a bluff overlooking the Missouri River, the A-Frame Winegarden at Les Bourgeois Vineyards is located in the tiny town of Rocheport, about 15 miles west of Columbia. The Bistro at Le Bourgeois and The Tasting Room are located nearby.

Two people drink wine on a patio overlooking the Missouri River at Les Bourgeois Vineyards near Columbia.
Sip award-winning wine on a blufftop patio at the A-Frame Winegarden at Les Bourgeois Vineyards near Columbia.

Springfield

Hike: Set out on the Greater Ozarks Audubon Trail at Lake Springfield to hike through woodlands and prairies. The 2.4 mile loop along the bluffs surrounding the lake includes a rocky overlook with views of the St. James River flowing into the lake.

Dine: Tucked away in the lower level of The Ozark Mill at Finely Farms, The Garrison offers elevated dining with river views. Located the town of Ozark, Finley Farms is about 15 miles south of Springfield. The original mill was built on the bank of the Finley River in 1833.

Celebrate: Indulge in a signature cocktail or local craft beer at Vantage Rooftop Lounge and Conservatory at Hotel Vandivort, a boutique hotel in downtown Springfield.

The Garrison at Finely Farms offers dinner and cocktails in a speakeasy atmosphere.
Experience fine dining with a speakeasy feel at The Garrison at Finley Farms in Ozark.

Branson

Hike: Experience the beauty of the Ozarks at the Lakeside Forest Wilderne­­ss Area, a short drive from downtown Branson. More than 5 miles of trails pass by rock formations and caves and offer sweeping views of Lake Taneycomo. A 315 stone-step path leads down to the lake’s edge.

Dine: Find regional fare and Ozark Mountain vistas at Top of the Rock’s Osage Restaurant at Big Cedar Lodge. The upscale wilderness resort is located 9 miles south of Branson.

Celebrate: Sitting high above Table Rock Lake, Top of the Rock’s Buffalo Bar offers breathtaking views – no rooftop necessary. Enjoy a handcrafted cocktail while you watch the seasonal sunset ceremony, featuring a bagpipe performance and the firing of a Civil War cannon.

Seating on the covered patio at Buffalo Bar at Big Cedar Lodge offers expansive views of Table Rock Lake.
Commanding views of Table Rock Lake take center stage at the Buffalo Bar at Big Cedar Lodge near Branson.