live music

Every weekend the Wayside and Larrick's Tavern brings you live music from all over the region and beyond!

  • Bluegrass Jam Session
    Multiple Dates
    Fri, Oct 07
    Wayside Inn & Larrick's Tavern
    Oct 07, 6:00 PM – 8:00 PM
    Wayside Inn & Larrick's Tavern, 7783 Main St, Middletown, VA 22645, USA
    Bluegrass Jam Sessions are held in the Senseney Ballroom every first Friday of each month! Wayside Inn welcomes all bluegrass lovers to enjoy a great meal while listening to their favorite musicians.
  • Wild West Show
    Sat, Oct 08
    Wayside Inn & Larrick's Tavern
    Oct 08, 10:00 AM – 6:00 PM
    Wayside Inn & Larrick's Tavern, 7783 Main St, Middletown, VA 22645, USA
    Wild West Show at Wayside Inn...come for the day. Bring your family & friends!
  • Jazz Night with Blackjack at the Speakeasy
    Multiple Dates
    Sat, Oct 22
    Wayside Inn & Larrick's Tavern
    Oct 22, 7:00 PM – 11:00 PM
    Wayside Inn & Larrick's Tavern, 7783 Main St, Middletown, VA 22645, USA
    Come and join us in the Speakeasy with a jazz night with Blackjack
  • Allen Boyd and the Waysiders
    Sat, Oct 29
    Wayside Inn & Larrick's Tavern
    Oct 29, 6:00 PM – 8:00 PM
    Wayside Inn & Larrick's Tavern, 7783 Main St, Middletown, VA 22645, USA
    A bluegrass event with Allen Boyd and the Waysiders.
  • Lonesome Ryder Band Halloween Costume Event
    Sat, Oct 29
    Wayside Inn & Larrick's Tavern
    Oct 29, 7:00 PM – 11:00 PM
    Wayside Inn & Larrick's Tavern, 7783 Main St, Middletown, VA 22645, USA
    A costume party, awesome buffet & great music by Lonesome Ryder Band. So dress up and celebrate this spooky holiday with the staff at Wayside Inn.
  • Shakin Woods
    Sat, Nov 12
    Wayside Inn & Larrick's Tavern
    Nov 12, 8:10 PM – 11:50 PM
    Wayside Inn & Larrick's Tavern, 7783 Main St, Middletown, VA 22645, USA
    Blues Night at the Speakeasy
  • Big Boy Little Band
    Sat, Nov 19
    Wayside Inn & Larrick's Tavern
    Nov 19, 8:00 PM – 11:10 PM
    Wayside Inn & Larrick's Tavern, 7783 Main St, Middletown, VA 22645, USA
  • New Year's Eve at Wayside Inn & Larrick's Tavern
    Sat, Dec 31
    Wayside Inn & Larrick's Tavern
    Dec 31, 2022, 7:00 PM – Jan 01, 2023, 2:30 AM
    Wayside Inn & Larrick's Tavern, 7783 Main St, Middletown, VA 22645, USA
    VIP Event in the Speakeasy lounge. includes 2 dinners and a room for Friday and Saturday, checkout on Sunday 11am. This ticket price is for a couple.