2026
Single hotel base - Sleeping at the same hotel for the entire tour, unpacking only once. Bicycling back to the base hotel half the days.
America's Longest Rail-Trail Adventure: Experience the Katy Trail State Park, the longest developed rail-trail in the United States at nearly 240 miles of smooth, crushed-limestone path—built on the historic Missouri-Kansas-Texas (MKT or "Katy") Railroad corridor, stretching from Clinton to Machens with 26 trailheads and four restored depots.
- Curated Daily Routes on the Best Sections: Ride the most scenic and iconic portions each day, covering highlights like river bluffs, farmlands, and charming small towns—perfectly paced for enjoyment without needing to tackle the entire length.
- Multi-Trail Prestige & Hall of Fame Status: Designated as part of the Lewis and Clark National Historic Trail, the American Discovery Trail, and a Millennium Legacy Trail; inducted into the Rails-to-Trails Conservancy Hall of Fame in 2008 for its exceptional design and impact.
- Stunning Missouri River Scenery: Pedal alongside the mighty Missouri River for miles of breathtaking views—towering limestone bluffs, lush floodplains, rolling farmlands, and peaceful woodlands—while passing through historic small towns that once bustled along the railroad tracks.
- Ideal for Every Rider: Bicycling reigns as the top activity on this mostly flat, car-free trail (with occasional hikers, equestrians, and backpackers allowed); expect gentle riding with frequent photo ops, benches, and wildlife sightings amid Missouri's diverse, ever-changing landscapes.
- Smart Wind-Proof Routing: Missouri headwinds? No problem—we've designed every day's route to be fully reversible! Simply flip the direction based on the forecast for tailwinds instead (because who doesn't prefer a gentle push over a battle?).
- Trail Surface Built for Comfort: Enjoy the firm, well-maintained crushed-limestone surface - suitable for most bikes, though we recommend hybrids, gravel bikes, e-bikes, or wider-tire models for the smoothest, worry-free ride.
- Unpack Once, Relax All Week: Settle into one comfortable hotel base for the entire trip - no daily packing or moving! Return each evening to the same spot for easy rest, recovery, and familiar amenities after your daily adventures.
- Effortlessly Flat & Accessible: Over approximately 160 miles of riding, encounter remarkably low elevation change - truly gentle and beginner-friendly, with an average gain that's minimal for rail-trail standards, letting you focus on the scenery, not the climbs!
Pricing options:
Economy $1799 per person/double occupancy (single occupancy +$450)
✔️Lowest price
✔️Pay Now
✔️No changes
✔️Non-refundable
✔️Limited price availability
Standard/Signature $2049 (the old-fashioned way*) per person/double occupancy (single occupancy +$450)
✔️Pay $200 deposit now
✔️Pay balance 45 days before trip start
✔️Full Credit for future trip for change or cancellation up to 60 days before trip start
✔️*This is the exclusive pricing way that Vacation Bicycling used for 18 years through 2024
Premier $2549 per person/double occupancy (single occupancy +$450)
✔️Pay with credit card or debit card
✔️Fully refundable/changeable up to 15 days before trip start
✔️No change fees
✔️Pay Now
Day 1, Sunday
Welcome Dinner
Start your Katy Trail bicycling vacation on Saturday in the welcoming capital city of Jefferson City, Missouri—a charming, mid-sized hub (population ~43,000, with a metro area of about 150,000–152,000) that's perfectly sized for easy exploration without feeling overwhelming. Situated midway between Kansas City and St. Louis along the mighty Missouri River, the city proudly bears the name of America's third president, Thomas Jefferson. Jefferson City boasts a rich history: Founded as the state capital in 1821, it served as a key Union stronghold during the Civil War, occupied early on by federal forces under General Nathaniel Lyon to secure Missouri for the Union. Today, its economy thrives on government, healthcare, manufacturing, retail, education, and tourism, creating a vibrant yet relaxed atmosphere.
Notable connections include Arthur Frommer, the legendary travel writer and founder of the iconic Frommer's guides (which sold over 75 million copies worldwide before the internet era)—he spent part of his childhood here during the Great Depression. Take time to discover Jefferson City's highlights: Marvel at the grand Missouri State Capitol, an architectural gem overlooking the river with stunning murals by Thomas Hart Benton, free tours, and the engaging Missouri State Museum inside. Nearby, admire the historic Missouri Governor’s Mansion (one of the oldest executive residences open to the public, with guided tours available seasonally—check ahead!), the elegant St. Peter Church adjacent to the Capitol grounds, and other nearby landmarks that showcase the city's beauty and heritage.
In the late afternoon, gather at your hotel at 4:00 pm for a friendly welcome meeting, followed by a delicious group dinner with new and returning rider friends. It's the perfect way to kick off your unforgettable week of pedaling along one of America's premier rail-trails—cheers to great rides, scenery, and camaraderie ahead!
Dinner:
Duke's on the Boulevard
- #1 Ranked Restaurant in the City by TripAdvisor -
Jefferson City, Missouri
Entrée Choices include:
- Ahi Tuna Salad - Seared rare tuna, cabbage, carrots, ginger vinaigrette, Yum-Yum, and wontons
- Duke's Specialty Smash Burgers - Brioche bun with choices including Duke's Original, The Frisco, Hangover and The Melt
- Blackened Atlantic Salmon - Honey glaze and steak butter served with your choice of two sides
- NOLA Pasta - Chicken breast, Andouille sausage, Alfredo, marinara & penne pasta
Lodging:
Hampton Inn Jefferson City
Jefferson City, Missouri
(Stay at the same hotel for the entire bicycle tour. Just unpack one time!)
- Internet
- Business Center
- HD TVs
- Fitness Center
- Coin Laundry
-
Indoor Pool
Day 2, Monday
Sedalia Depot/Clifton City Trailhead to Boonville Trailhead
Today’s first full riding day launches your Katy Trail adventure after a scenic van shuttle to the premier starting point: the beautifully restored Sedalia Katy Depot trailhead—one of the trail's most iconic and historic spots. Listed on the National Register of Historic Places since 1979, this grand passenger depot (fully restored in 2001) once welcomed travelers on the Missouri-Kansas-Texas (MKT or "Katy") Railroad for decades. Take a moment to explore its exhibits, gift shop stocked with Katy Trail memorabilia, and Railroad Heritage Museum—it's the perfect spot to soak in the railroad's rich legacy before you clip in and roll out.
From Sedalia (mile marker ~229), you'll pedal northeastward on smooth crushed limestone toward Boonville, covering roughly 35–40 miles of gentle, mostly flat terrain (with a slight overall downhill trend in this direction). This leg stands out as the only section where the Katy Trail crosses the mighty Missouri River—you'll glide high over it via the adjacent roadway bridge (with views of the historic rail bridge nearby, currently under preservation efforts to maintain the corridor). Along the way, enjoy classic Missouri scenery: wide-open farmlands, rolling plains, peaceful woodlands, and vintage railroad cars displayed at various trailheads. Pass through quiet whistle-stop communities like Clifton City and Pilot Grove, remnants of the railroad era that add charm and historical flavor.
Your destination is charming Boonville (mile marker ~191.8), a historic river town named for the legendary frontiersman Daniel Boone. Its strategic spot on the Missouri River made it a hotly contested prize during the Civil War—site of the First Battle of Boonville (June 17, 1861, one of the war's earliest land battles) plus additional engagements and occupations. Today, Boonville welcomes Katy riders with its restored Katy Depot (a rare surviving Spanish Mission-style structure from 1911–1912, also on the National Register, now housing a chamber office and bike shop), nearby museums, and easy access to downtown delights. This relaxed, scenic opener sets the tone for the week—plenty of photo ops, benches for breaks, fresh air, and the pure joy of pedaling a car-free rail-trail through Missouri's heartland. End your day with a well-earned rest at your hotel base, ready for more adventures tomorrow!
Breakfast provided by the hotel each morning.
Bicycling Route: On the Katy Trail:
- 0 miles, staying at the hotel or
- 24 miles, riding from Clifton City Trailhead to the Boonville Trailhead or
- 35 miles, riding from the Sedalia Depot Trailhead to the Boonville Trailhead.
- [The routes are primarily on a rail trail and are basically flat; the route from North Jefferson to the hotels has some hills and road riding.
Dinner:
El Jimador
Jefferson City, Missouri
Entrée Choices include:
- Fajitas - Chicken, Steak, Shrimp of Vegetarian served sizzling hot
- Santa Fe Chicken - Chicken breast delicately seasoned and grilled to perfection, topped with grilled onions, mushrooms, tomatoes, bell peppers and jack cheese.
- Quesadilla - Chickens, Steak, Sausage or Shrimp
- Taco Salad - Crisp flour tortilla filled with beef or chicken over fresh lettuce with cheese, sour cream guacamole and tomatoes
Day 3, Tuesday
Boonville/Rocheport Trailhead to North Jefferson City Trailhead/hotel
Today’s ride picks up right where yesterday left off, with a convenient van shuttle option to either Boonville (where we finished the previous day) or the charming Rocheport trailhead—allowing you to customize your start and savor one of the Katy Trail's most celebrated and scenic sections. From Boonville (mile marker ~191.8), pedal eastward through open farmlands, shady tree canopies, and peaceful river views before reaching Rocheport (mile marker ~178.3), a picturesque historic town with quaint shops, eateries like the popular Meriwether Café & Bike Shop, and trailside charm. If starting in Rocheport, you'll dive straight into the highlight: the iconic Rocheport Tunnel—the only tunnel on the entire 240-mile Katy Trail. This impressive 243-foot-long (approximately 240-foot) limestone passage was blasted through solid rock in 1892–1893 by the Missouri-Kansas-Texas Railroad to bypass frequent Missouri River flooding in the area. Today, it's a cool, atmospheric highlight—perfect for photos, a brief walk-through, and marveling at the engineering that made the original rail line possible. Emerging from the tunnel, enjoy dramatic limestone bluffs rising alongside the trail, sweeping views of the Missouri River, lush woodlands, and the ever-changing Missouri countryside.
Continue northeastward on the smooth crushed-limestone path toward Jefferson City, passing through serene stretches with wildlife sightings, benches for breaks, and historical markers that nod to the trail's railroad heritage (including ties to the Lewis and Clark expedition nearby). The route ends at the North Jefferson City Trailhead (conveniently close to your hotel base), wrapping up a relaxing ~35–40 mile day (depending on your exact start point) of gentle, mostly flat riding. This leg captures the essence of why the Katy Trail is a Hall of Fame favorite—stunning natural beauty, historic gems like the tunnel, and the pure pleasure of car-free pedaling along America's longest rail-trail. Return to your familiar hotel for rest, recovery, and anticipation of tomorrow's miles!
Breakfast provided by the hotel each morning.
Bicycling Route: On the Katy Trail:
- 0 miles, staying at the hotel or
- 35 miles, riding from the Rocheport Trailhead to the North Jefferson City Trailhead or
- 49 miles, riding from the Boonville Trailhead to the Jefferson City Trailhead or
- 61 miles, riding from the Boonville Trailhead to the hotel
- [The route are on a rail trail and are basically flat]
Dinner:
On your own
New Day 5, Wednesday
McKittrick Trailhead to Augusta Trailhead
Today’s third day on the Katy Trail reverses the flow for a fresh perspective, starting from the quiet McKittrick trailhead (mile marker ~100.8) and pedaling southwestward toward the historic hamlet of Augusta (mile marker ~66.3)—a delightful ~34-mile leg of gentle, mostly flat crushed-limestone riding that hugs close to the Missouri River for much of the journey. Begin in peaceful McKittrick, a low-key trailhead with parking, restrooms, a bike repair station, and easy access. As you roll out, enjoy serene rural Missouri scenery: open farmlands and pastures, lush shaded canopies of trees, peaceful river overlooks, and the occasional glimpse of wildlife amid the floodplain and rolling countryside. The route follows the historic rail corridor closely along the Missouri River valley, offering tranquil views of the water, limestone bluffs in the distance, and the ever-changing patchwork of fields and woodlands. Frequent benches provide perfect spots for breaks, photos, or simply soaking in the calm—it's classic Katy Trail relaxation with minimal elevation change and no major climbs to interrupt the flow.
Your destination is charming Augusta, nestled in the heart of Missouri's pioneering wine country—the nation's very first official American Viticultural Area (AVA), established in 1980 (predating Napa Valley's designation). Founded in 1836 as a river landing, Augusta grew into an agricultural hub for grain, livestock, and especially wine grapes from 19th-century vineyards. German immigrants helped shape its winemaking legacy, with historic gems like Mount Pleasant Winery (est. 1859) still thriving today. Despite its small population (~270), this welcoming spot boasts its own public library, multiple wineries with scenic terraces and tastings (including Augusta Winery right near the trail), antique shops, galleries, and a cozy vibe ideal for Katy riders. This reversed direction delivers the same stunning natural beauty and historic charm but with a southwestward flow that often catches favorable winds and a different lighting on the river views. Wrap up at the Augusta trailhead, then shuttle back to your comfortable hotel base for rest, recovery, and looking forward to tomorrow's miles. This segment perfectly showcases the Katy Trail's magic: effortless pedaling, river-hugging serenity, and a taste of Missouri's rich wine heritage!
Breakfast provided by the hotel each morning
Bicycling Route: On the Katy Trail;
- 0 miles, staying at the hotel or
- 34 miles, riding from the McKittrick Trailhead to the Augusta Trailhead
- [The routes are on a rail trail and are basically flat]
Dinner:
On your own
Day 6, Thursday
McKittrick/Portland Trailhead to North Jefferson City Trailhead/hotel
Today’s ride continues your westward journey on the Katy Trail, with a convenient van shuttle back to the McKittrick trailhead (mile marker ~100.8) where we wrapped up the previous day. From here, pedal southwestward toward North Jefferson City (mile marker 143.2), covering a relaxed ~42–45 miles of gentle, mostly flat crushed-limestone path—classic rail-trail riding with minimal elevation change and plenty of opportunities to enjoy the scenery at your own pace.McKittrick itself is a quiet, former railroad town whose existence and modest heyday were tied directly to the Missouri-Kansas-Texas (MKT or "Katy") Railroad—remnants like old depot foundations and coal sheds still linger at the trailhead as subtle nods to its past.
As you roll along, you'll pass through several small, historic trailheads that offer glimpses of once-thriving railroad communities: Portland (mile marker ~115.9, a peaceful spot with parking and basic amenities), Mokane (often noted for its historic grain elevators still in use), and Tebbetts (mile marker 131.2, another low-key stop with restrooms and a sense of rural Missouri charm). These quiet whistle-stops highlight the trail's heritage—small towns that grew up around the tracks, now serene waypoints with benches, occasional wildlife sightings, and open views of farmlands, woodlands, and the nearby Missouri River. The route hugs the river valley for much of the way, delivering peaceful river overlooks, shaded canopies in spots, and the ever-changing patchwork of Missouri's countryside. This section includes the equestrian-friendly stretch between Portland and Tebbetts, adding to the trail's multi-use appeal.
Your ride concludes at the North Jefferson Trailhead—roughly the midpoint of the entire 240-mile Katy Trail—conveniently close to your hotel base and with easy views of the iconic Missouri State Capitol dome rising across the river. A short spur or pedestrian bridge crossing lets you access downtown Jefferson City if you'd like to explore more. By the end of today, you've pedaled the majority—and many consider the most scenic and iconic—portions of America's longest developed rail-trail. Celebrate with a well-deserved rest at your familiar hotel, reflecting on the river views, historic echoes, and effortless miles that make the Katy such a legendary ride!
Breakfast provided by the hotel each morning
Bicycling Route: On the Katy Trail:
- 0 miles, staying at the hotel or
- 27 miles, riding from the Portland Trailhead to the North Jefferson City Trailhead or
- 43 miles riding from the McKittrick Trailhead to the North Jefferson City Trailhead or
- 55 Miles riding from the McKittrick Trailhead all the way to the hotel.
- [The routes are primarily on a rail trail and are basically flat; the route from North Jefferson to the hotel has some hills and road riding.]
Dinner:
Oscar's Classic Diner
- The most popular, most awarded and busiest restaurant in Jefferson City, since 2004 -
Jefferson City, Missouri
Dinner choices include:
-
Fish & Chips - Golden brown catfish fillet served with homemade chips and tartar sauce.
-
Chicken Penne Carbonara - Sautéed mushrooms, crumbled bacon and tender chicken in Oscar's rich cream sauce
- Sirloin Steak - One of Oscar's most flavorful steaks, naturally firm and lean.
- Grilled Chicken Salad - Tender chicken marinated and grilled to perfection, layered on a bed of fresh mixed greens, tomatoes, red onion, cheddar and mozzarella
- Fresh Harvest Strawberry Salad - A fresh harvest blend topped with onions, sliced strawberries, peans and crumbled blue cheese with grilled or crispy chicken
Day 7, Friday
Bicycle one last time on your own before departing for home.
Breakfast provided by hotel each morning
Please note all trip information is based on previous trips and/or contracted lodging and restaurants and is subject to change based on availability or specific trip needs.
Riding difficulty:
-
Riders who are comfortable riding at least 10 miles per hour should have an enjoyable trip. The routes are all on the designated Katy Trail Bike path. Please see the daily routes descriptions for additional information. Of course, if a rider is tired or does not feel like riding, the SAG vehicle will transport the rider. All riders may ride at their own pace, slow or fast or anything in-between.
-
The Katy Trail is on crushed limestone. The trail is normally in very good shape for all bikes; though e-bikes, hybrid bikes, mountain bikes, gravel bikes or bicycles with wider tires are recommended.
Arriving by Automobile:
- Drive to the starting hotel: Hampton Inn Jefferson City, 4800 Country Club Dr, Jefferson City, Missouri
Arriving by Plane:
- Fly into the Columbia, Missouri Regional Airport (COU) and rent a car or take an airport shuttle (such as W&WSRT Shuttle) for the for the 26 minute drive to the hotel. Some people may choose to fly into the St. Louis International Airport (STL) and rent a car for the 1 hour 50 minute drive to the hotel.
Deposit:
- $200 to reserve your spot and the remainder due 45 days before the trip start.
What is Included:
- Hotel lodging
- Ride Packets with Cue Sheets (directions)
- Garmin/GPS routes to download
- Google Maps routes for your iPhone or Android Phone
- Fully sagged including van transportation and rider assistance.
- Breakfast each morning
- Happy Hours (BYOB) on selected evenings
- Dinner with the group twoevenings (see above)
- Great riding, scenery, fun and enjoyment!
Bicycles:
-
Most participants bring their own bicycles
-
To ship your bike, we would suggest using shipbikes.com or bikeflight.com for shipping. To ship your bike to the hotel: Hampton Inn Jefferson City, 4800 Country Club Dr, Jefferson City, MO 65109
-
If you fly, many major airlines including now waive the oversize fee for bicycles (sporting equipment) and just the standard luggage fee applies. Please contact your airline for all the details.
-
Bike Rental: Bikes are available for rent in the area, including Red Wheel Bike Shop in Jefferson City; or Pedego in Columbia that rents e-bikes. We suggest conducting a Google search in Jefferson City or in nearby Columbia to find the best place to accommodate your needs.
Weather on the Katy Trail area at the time of trip:
- Average High: 69°