Plan A Fall Adventure Weekend With Us!

Go ”Back to School” this Fall! Autumn weather is coming and we are already experiencing some welcome relief from summer’s heat. Fill your weekend with antiques, wineries, coffee, pumpkins and mums! We know all the best places and would love for you to stay with us.

For many this time of year we want to be filled with sights, sounds and smells of the season. What better way than to plan an amazing weekend filled with all of your favorite things. Pack your blue jeans and sweaters and plan to enjoy the best of the season. Our great rates allow you to spend the rest of your money on all the things you want to enjoy. There are places to buy pumpkins or mums to fill your front porch, delicious coffee to sip and stay warm on a cool afternoon, gift shops, distilleries, lovely wineries, live music and gorgeous lakes and riverfronts. The corridors of Highways 100 and 50 are loaded with beautiful scenery and amazing places to stop and shop. Our B&B is in the middle of it all and we get you off to a great start with a restful night’s sleep and a full breakfast each morning.

Coming in from the Kansas City area, St Louis, out of state? We are in the perfect location for you to reach so many destinations within an hour drive. Plan your trip and we can show you how to visit some sweet mid-Missouri destinations and save money on fuel! There is no reason you can’t have it all. You can even get a better rate if you have a group, and it is so much fun! Call us to get the scoop.

Check out what you will find along Hwy 100:

  • Washington, MO – James W Rennick Riverfront (walk, pavilion, boat launch), City Park (Lions Lake walk and picnic area), Farmers Market, Sugarfire Smokehouse, Oak & Front Wine Bar, 1869 Draft Room, underGrounds Expresso Bar, Washington Coffee Shop, Iron Spike Model Train Museum, October Pumpkin Palooza.
  • New Haven, MO – Elizabeth’s Gift Shop, Walt Theater, Astral Glass Studio, Wolf Ferry Wine Bar, Pinckney Bend Distillary, Riverfront walk
  • Hermann, MO – Oak Glenn, Stone Hill, Adam Puchta, Martin Bros Wineries, Stompin Grounds and Expresso coffee houses, antique stores and restaurants (visit Swiss for great sausages) You can experience Oktoberfest in Hermann all weekends in October!
  • Chamois, MO – Old School on the Hill B&B (that’s us), Riverfront boat access, pavilion and camping, Roomerz Bar & Grill, Ben Branch Conservation area lake, ”Boys from Chamois” roadside shack with pumpkins.
  • Osage County also has Westphalia Vineyard Norton Room and Wenwood Farm Winery with ”Tunes in the Afternoon” in October

There is even more along Hwy 50:

  • Rosebud, MO – they have their Miracle Mile of antiques and food. Check out the Grand Antique Mall open Sept 9th only – for beautiful antiques that are reasonably priced!
  • Linn, MO – Old School Antique Mall consignment shop/flea market & coffee shop, restaurants (Mexican, Wings, Pizza)
  • Frankenstein/Bonnets Mill, MO – Countryside Gardens – with the biggest mums you will ever see and pumpkins galore
  • Loose Creek, MO – visit The Hatchery for homemade and antique items, open Sundays
  • Jefferson City, MO – Jail Tour (also haunted ones!), Jail Museum, Central Dairy Ice Cream Parlor


  • 2-5 (includes Labor Day)
  • 9 – 11 (the 10th is when the Rosebud Grand Antique Mall is open)
  • 16-18 (this is Chamois Day weekend, our town celebration)
  • 30 – 10/2
  • To reserve for September click here
  • 9/30 – 10/2
  • 7 – 10
  • 14 – 16
  • 21 – 23
  • 28 – 30
  • To reserve for October click here


Our Inn has 4 large rooms (750 sq ft) so you have a lot of private space with a bath ensuite in each room. Three of our rooms are outfitted with King beds, sitting area, coffee & tea service in the room, and great views. One of our rooms is unique in that it has two full size beds and an extra twin – a great option for a small ladies group that really wants to save $$ to buy all those extras on the trip! You will visit yesteryear in our old school converted to a B&B. We have been her Innkeepers for the last 8 years and we look forward to welcoming you!

There are so many things to do in mid-Missouri this Fall, let us help you plan your stay and magical adventures for the weekend!

Come stay with the ”best in class” for your adventure! See you soon!

We are your Innkeepers, LeRoy & Debbie Huff. We’ve owned the Old School for 8 years and love meeting our guests.

You can find us on Facebook at @oldschoolonthehillbandb for more pictures, updates, address and information!

Good food, good sleep, and lively conversations! We would love to see you soon, come connect with us!

402 South Main Street / Chamois, MO