Middletown Holidays

This historic fairgrounds combines a century-old county fair with thrilling dirt track racing. Enjoy carnival rides during the July fair or catch heart-pounding motorsport action at the legendary speedway.

Explore 3,000 acres of pristine wilderness at this undeveloped sanctuary for outdoor enthusiasts. Hike forest trails, cast a line in serene lakes, or ride horseback with a permit through untouched nature.

Discover 3,115 acres of pristine wilderness with informal trails winding through forests and around lakes. Bring supplies for horseback riding, fishing, or hiking in this peaceful, undeveloped natural retreat.

America's oldest continuously operating dirt track, Orange County Fair Speedway has thrilled racing fans since 1919. Experience the roar of engines and excitement of dirt track racing at this historic motorsport venue.

The Galleria at Crystal Run offers over 100 stores and entertainment venues in the heart of Middletown. Explore premium retailers like Macy's or catch a film at the cinema for a complete shopping experience.

This 1929 theatre boasts Carnegie Hall-like acoustics, hosting diverse performances in its intimate 1,100-seat venue. Experience cultural richness through concerts, films, or shows in this historic Middletown gem.

Enjoy the student vibe at Orange County Community College during your stay in Middletown. While in this family-friendly area, you can savour the top-notch restaurants.