Entertainment and Events – We Are The Hub Of Everything Skagway

From thrilling competitions to one-of-a-kind entertainment, we are proud to host regular events and night time music for locals and visitors alike. Our Corn Hole Arena is open all day, and everyone is invited to grab some bags and brew and take part in some friendly competition. If you like live music, dancing, and events that are truly Alaskan, we offer fun and frivolity throughout the summer and winter seasons.

Check back regularly for music and entertainment updates. What follows is an overview of our many exciting offerings.

  • Weekly Corn Hole Tournaments – Single elimination competitions take place on Friday nights. Two person teams compete for prizes that include a $50 gift certificate to the Happy Endings Saloon for First Place.
  • High Stakes Corn Hole Tournaments – Throughout the summer, a $50 entry fee allows two-person teams to compete for prizes that include $500 worth of gift certificates for First Place, and $300 in Gift certificates for Second Place.
  • Last Ship Day Corn Hole Tournament – On the last official day of the cruise ship season, this special tournament starts at 6pm. Entry fees are $20 per team, and First Place gets a $100 gift certificate to The Station Bar & Grill or the Happy Endings Saloon.
  • Fourth of July – Multiple events throughout the day makes us the hub of celebration during Skagway’s famous celebration of America’s birthday. The fun starts on the 3rd with our Midnight Street Party, that lasts until midnight and features live music and a fun Singles Corn Hole Tournament. The excitement starts back up at 8am on the 4th, with our Annual Block Party with food and beverage specials, live music, and corn hole tournament excitement. Don’t miss our infamous Hot Dog Eating Contest and a rotation of Skagway’s hottest bands playing local music on our outdoor stage.
  • Original Game Shows – During the winter months, contestants compete for fabulous prizes in a variety of game show formats. Play as a contestant or watch the excitement as our talented MC hosts Skagway Jeopardy, Dysfunctional Family Feud, and The Not-So-Newlywed Game, among others.
  • The Lake Nona Pig Run – This 5K run through Skagway raises money for families with children diagnosed with chronic of life-threatening conditions. This run originated in Orlando and we joined the cause in 2013. This is one of our Skagway runner’s favorite races because of the bacon and donuts served at the end of the race.
  • Finding Hup 5K – This race is held on Saturday August 20, 2016 and the entry fee is $20. Finding Hup is a charitable organization that raises money for athletes with special needs that require special equipment to enjoy an active lifestyle.
  • Turkey Trot – This 5K race is held annually on Thanksgiving morning at 10am and is the perfect way to get into the holiday spirit. 2016 marks the 15th year of this popular local event. The entry fee is $10 and all proceeds go the Skagway High School Booster Club. First Place male and female winners win a homemade apple pie!
  • Local Music – Skagway’s local music scene is rich and diverse, so check the Happy Endings for nightly updates on local bands and DJs playing on Skagway’s only indoor stage.