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Wayside Inn

Middletown, VA View map Visit website


Wayside Inn is a wedding and event venue located in Middletown, Virginia. First established in 1797, this property is the oldest inn in the U.S. that's still in operation. The historic, vintage atmosphere shines through each detail, from the outdoor patio to the cozy overnight rooms.

Facilities and Capacity

Wayside Inn is located in a peaceful setting that's ideal for couples seeking a retreat from the fast-paced city life. The main doors lead to multiple peaceful seating areas, adorned with vintage furniture, chandeliers, and a red-brick fireplace for a warm, welcoming aesthetic.If you prefer an outdoor setting, a brick patio offers plenty of space for you to enjoy your ceremony, cocktail hour, or reception. Grassy lawns and lush gardens surround the space for a picturesque setting. Right beside the patio is a covered event area for you to enjoy a rustic-themed celebration. Exposed wooden beams and intimate lighting decorates the vaulted ceiling for a down-to-earth atmosphere. In addition, the inn features 22 guestrooms for you and your guests to enjoy a relaxing wedding weekend.

Services Offered

Wayside Inn features an in-house event planner who will work closely with you to help you complete your wedding day.

Frequently Asked Questions

Describe your venue:

Historic Building

What kind of settings are available?

Covered Outdoor
Uncovered Outdoor

Which of the following wedding events does your venue service?


What event services do you offer?

Event Planner
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Any other questions?

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out of 5.0
Recommended by 90% of couples
  • Quality of service
    4.5 out of 5 rating
  • Average response time
    4.5 out of 5 rating
  • Professionalism
    4.5 out of 5 rating
  • Value
    5 out of 5 rating
  • Flexibility
    4 out of 5 rating
  • R
    Brian Married on 08/05/2008
    4.5 out of 5 rating
    • Quality of service
      4.5 out of 5 rating
    • Responsiveness
      4.5 out of 5 rating
    • Professionalism
      4.5 out of 5 rating
    • Value
      5.0 out of 5 rating
    • Flexibility
      4.0 out of 5 rating
    The Wayside Inn did it al for us and in 6 weeks! from the ceremony in the garden to the reception in the historic Inn they did it all in with style. Would you believe they are affordable as well?
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7783 Main Street Middletown, VA, 22645
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