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Trail Rides – 3 Unique Experiences Near Annville Inn

Trail Rides – 3 Unique Experiences Near Annville Inn

Published on August 16, 2025 On Day Trips, Hershey Area Adventures, Outdoor Activities and Exploring, Top Things To Dop Near Annville Inn

Whether you’re a first-time rider or a seasoned equestrian, Pennsylvania offers breathtaking horseback riding experiences that combine natural beauty, rich history, and good old-fashioned fun. If you’re looking to saddle up and explore scenic trails and tranquil woodlands, we’ve got three unforgettable trail rides for you to check out near us:

Image of Stone Gables Estate Horse enclosure for horseback trail rides.

1. Stone Gables Estate – 250+ Acres

Nestled just 15 minutes from both Lancaster and Hershey, Stone Gables Estate offers a peaceful, one-hour guided trail ride through 275+ acres of pristine forests and open fields. This isn’t just a horseback ride, it’s a step back in time.

Why You’ll Love It:

  • Gentle, well-trained horses make it perfect for beginners.
  • Gorgeous scenery around every bend.
  • As well as professional guides who provide a pre-ride demonstration to ensure safety and comfort.
Image of a couple on a trail ride.
Image of a couple horseback riding.

Information:

  • All riders must be 8 years or older.
  • No experience needed.
  • Helmets required for riders under 18 (provided) as well as closed toed shoes for all riders

Book online or call 717-413-2660 (office closed Sundays and Mondays).

2. Hickory Hollow Farm – A Ride Through the Gettysburg Battlefield

Image of a trail ride through Gettysburg Battlefield.

If you’ve ever wanted to experience history on horseback, Hickory Hollow Farm in Gettysburg offers something truly special: guided trail rides through the actual Gettysburg Battlefield. Operating for over 30 years, this family-run farm brings history to life in the most memorable way.

Image of a horse used for trail rides.
Image of the scenery on a trail ride through Gettysburg Battlefield.

What to Know:

  • Riders must be at least 7 years old, and under 250 lbs.
  • Prior riding experience not needed.
  • Helmets required for ages 7–17 (provided) as well as long pants and closed-toe shoes for all riders.
  • Rides happen rain or shine, as long as it’s safe. If weather cancels your

tour, you’ll receive a full refund.

To book, call 717-253-6300. Tours run April through October.

3. Winsome Farms – Scenic Rides Year-Round in Newville

Looking for a laid-back, flexible horseback riding experience? Winsome Farms in Newville offers daily trail rides across 50 acres of pastures and woodlands, as well as access to the stunning 13-mile Cumberland Valley Rail Trail.

What Makes It Special:

  • Great for beginners and families.
  • Daily rides at 11 AM, 1 PM, and 3 PM.
  • Beautiful year-round scenery as well as a peaceful atmosphere.

Information:

  • Riders must wear closed-toe shoes as well as long pants.Call ahead to schedule a ride (contact info available on their site).
  • Information:
    Riders must wear closed-toe shoes as well as long pants.
    Call ahead to schedule a ride (contact info available on their site).

Enjoy your stay here at Hershey’s Five Star Annville Inn, famous for

  • Rosalie’s breakfasts and hospitality
  • Our quiet country elegance
  • Amazing views…

And more amenities than most inns: 

  • Full sized in-ground swimming pool
  • Six-person hot tub
  • 20-seat movie theatre with Dolby 7.1 Surround just like at the “movies”
  • Plant conservatory glassed in on all sides with a wood burning fireplace for winter
  • Three acres of botanical gardens with over 600 roses and 10,000 bulbs. 
  • Large game room with pool table
  • Three dining areas for breakfast,
  • Jacuzzis in Guest Rooms,
  • Most rooms with private entrances and decks
  • Fireplaces in all rooms
  • King and queen beds throughout
  • …and much more to enjoy at Annville Inn!

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Annville Inn News – January 2026 Valentines Edition
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Categories

  • Annville Inn News
  • Arts Scene in the Area
  • Concerts in Hershey, PA
  • COVID-19
  • Day Trips
  • Events At the Inn & In Our Region
  • Hershey Area Adventures
  • Hershey Area Hikes and Walks
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  • Indoor/All Season Activities
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  • News around the Inn
  • Outdoor Activities and Exploring
  • Outdoor Sports near Hershey
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  • Top Things To Dop Near Annville Inn
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4515 Hill Church Rd., Annville, PA 17003

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