October 4-5, 2019

Medora, ND

The wine industry in the Dakotas and Eastern Montana has grown over the last several years!
Wines produced by those wineries will be showcased in Medora on October 4-5, 2019!

Wine, Cheese and Live Music

Lots of Wine

Welcome Reception, Dinner, Sip 'n Paint and Festival

Friday Night the focus is solely on North Dakota Wines! Paired with the Welcome Reception Appetizer, Three Course Dinner and then the "sipping" part of Sip 'n Paint, you will surely get a nice taste of what North Dakota Wineries have to offer! Saturday at the Main Festival, there will be wineries from North Dakota, South Dakota and Montana providing tastings as part of the entry into the Festival.

Cheese and Light Hors d'oeuvres

Festival Snacks

We welcome Wild Vines Market from Beach, ND, who will be providing a cheese and light hors d'oeuvres table during the Festival! Cheeses featured will be from Dimock Dairy in Dimock, SD!

Friday Night Live Music

Connie Gjermundson

A western North Dakota native, Connie Gjermundson has been passionate about country life and country music all her life.

Since first performing at the age of five, she has taught herself a variety of instruments and immersed herself in writing original music as well as playing popular standards. Her single “Ride For Eight Seconds” is currently the theme song of “Wild Rides” on The Cowboy Channel.

Gjermundson infuses her country music with a sampling of folk and blues while lifting her fans with a high energy performance. She is inspired by her own life lessons and the blessings she’s found in raising four children.

Music has been and will continue to be a healing force for Gjermundson. Connie says she can forget about her troubles when she’s playing and singing. She writes about a wide range of life experiences, and feels great joy when others tell her how her music has touched them.

Saturday Live Music

Alyssa Scott

Singer/Songwriter Alyssa Scott, a northern girl with a southern soul, is originally from Fargo, ND and grew up in Minnesota with the wild north spirit. Influenced by many artists at a young age, Alyssa knew she was going to make a career in writing and performing.

She moved to Minneapolis, MN where she received a degree in Vocal Performance from McNally Smith College of Music. After school, she has continued to pursue her career in music by fronting many cover bands and spending time recording with influences, Sean Turner and Phil Solem from the Rembrandts. Alyssa performed in the Medora Musical for two years before now residing full-time in Nashville, TN.

Alyssa is now a Nashville Recording Artist maintaining original shows showcasing her art. She recently released her first single “Back Home”.


A detailed description of each event.

6:30 PM


  • Welcome Reception
Welcome to Medora! The North Dakota Wine Industry welcomes guests with an appetizer and paired North Dakota wine. Winemakers from around North Dakota will be mingling while everyone is seated for the three-course dinner. Advance ticket purchase required for the welcome reception and dinner.

7:00 PM


  • Three-Course Dinner
With a menu prepared by Little Missouri Saloon and wines provided by North Dakota wineries, guests will enjoy a plated three-course dinner along with delightfully paired wines. Check back often as the menu and specific wines are being finalized. As guests are finishing up dinner, Connie Gjermundson will entertain the group with Live Music.

9:30 PM


  • Sip 'n Paint After Dark
Just when you thought drinking wine couldn't get any more fun, we welcome you to join in this evening activity! Led by Kristin Morel, an Independent Chalky & Co. Representative, attendees will be able to paint "The Winery" - a wine box while enjoying North Dakota wines. Advance ticket purchase required.

12:00 PM


  • Main Festival
Some will refer to this as "The Main Event" and there is a reason for that - welcoming several wineries from North Dakota, South Dakota and Montana, attendees will be able to enjoy tastings from each winery, as well as cheese from Dimock Dairy, SD prepared by Wild Vines Market in Beach, ND! While guests are enjoying wine tastings, Alyssa Scott will be providing Live Music.

1:30 PM


  • Sip 'n Paint
For guests attending just the Saturday festival who wish to do some fun painting while enjoying the tastings, Kristen Morel, Independent Chalky & Co Representative, will be conducting another Sip 'n Paint with "The Winery" - a wine box. Sipping for this Paint 'n Sip is part of the samplings during the Festival. Advance Ticket purchase required.

Ticket Packages and Prices


All-Inclusive for One



  • 1Welcome Reception/Dinner
  • 1Sip 'n Paint After Dark Ticket
  • 1Night Lodging
  • 1Main Festival Ticket
  • Special Discounts at Medora Uncork'd
Best Deal

All-Inclusive for Two



  • 2Welcome Reception/Dinner
  • 2Sip 'n Paint After Dark Tickets
  • 1Night Lodging
  • 2Main Festival Tickets
  • Special Discounts at Medora Uncork'd

All-Access for One
(No Lodging)



  • 1Welcome Reception/Dinner
  • 1Sip 'n Paint After Dark Tickets
  • 1Main Festival Tickets
  • Special Discounts at Medora Uncork'd

Welcome Reception/


per person

  • 1Ticket
  • Welcome Reception with Appetizer & Paired ND Wine
  • Three-Course Dinner with Paired ND Wine for each Course
  • Live Music following Dinner

Sip 'n Paint After Dark (Friday)


per person

  • 1Ticket
  • Choice of Wine Box or Wine Glass/Bottle Holder w/2 Colors
  • Wines from North Dakota Wineries

Main Festival (Saturday)


per person

  • 1Ticket
  • Tastings from each of the Participating Wineries
  • Cheese Table w/Light Hors d'oeuvres
  • Live Music

Sip 'n Paint (Saturday)


per person

  • 1Ticket
  • Choice of Wine Box or Wine Glass/Bottle Holder w/2 Colors

Buy Tickets Now

The Friday Night activities and special lodging rates must be pre-purchased and space is limited! Purchase your tickets today!


Festival Sponsors

Organizing Sponsor

Medora Uncork'd

Medora Uncork'd is Western North Dakota's premier wine bar!

Lodging Sponsor

AmericInn by Wyndham - Medora

Experience all that western North Dakota has to offer with a stay at AmericInn Lodge & Suites Medora. Conveniently located minutes from I-94, our hotel is in the heart of scenic Medora and close to Little Missouri National Grassland and Theodore Roosevelt National Park. We are the perfect site to stay and enjoy the world-famous Medora Musical, held each summer at Burning Hills Amphitheater, less than 2 miles from our lobby doors.

Dinner Catering Sponsor

Little Missouri Saloon

Medora's oldest continual Saloon and Steakhouse. Enjoy the brand new outdoor deck seating! Large menu including sandwiches, steaks, burgers and fresh made pizza. Full-service saloon with a large variety of craft beers.