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Guided trail rides in Massachusetts

31 stables in Massachusetts offer guided trail rides, out of 373 stables we list in the state. Each one is here because a customer review or its own website mentions guided trail rides, and the proof is under each stable.

31Stables
28Cities
373All stables in MA

Top 12 by rating and reviews

Ranked by Google rating × number of reviews (10 reviews or more). The other 19 stables are listed by city below.

Open-now times come from Google; call the stable before you go.

Cornerstone Ranch

Cornerstone ranch

Trail ridesLessonsBeginners
4.8Rating
948Reviews
7Services

The wranglers were confident and made us feel at ease.

From a Google review

Bobby's Ranch

6 Durkee Ln

Trail ridesLessonsBoarding
4.7Rating
323Reviews
5Services

I really loved the trail ride.

From a Google review

The stable's website says so too.

Blazing Saddles Equestrian Center

384 High St rear

Trail ridesLessonsBeginners
4.3Rating
175Reviews
5Services

Our trail guide was fantastic, they shared so much information about the horses, answered all of our questions, and made the ride even more enjoyable.

From a Google review

Meeting House Farm and Sanctuary

333 Quaker Meetinghouse Rd

Trail ridesLessonsBeginners
4.4Rating
59Reviews
4Services

I have came over 5 times for guided trail rides and every time it gets better!

From a Google review

The stable's website says so too.

Berkshire HorseWorks

101 Patton Rd

Trail ridesLessons
5Rating
42Reviews
2Services

My husband and I decided to do a trail ride experience with Berkshire HorseWorks and it truly was an unforgettable and amazing time.

★★★★★ Arielle, Jun 2023

HomeFarm at Undermountain

400 Under Mountain Rd

Trail ridesLessonsBoarding
4.7Rating
43Reviews
6Services

I did a trail ride here and had the best time ever!

From a Google review

Horse stable

286 South St

Trail ridesLessonsBoarding
5Rating
31Reviews
5Services
Trail rides: per the stable's website

The Dale Perkins Horse Show

67 Muschopauge Rd

Trail ridesLessonsBeginners
4.9Rating
31Reviews
5Services
Trail rides: per the stable's website

A J Stables

1040 E Mountain Rd

Trail ridesLessonsBoarding
4.9Rating
24Reviews
6Services

I went on my first horseback trail ride.

From a Google review

Cranberry Sunset Farm

1964 Main St

Trail ridesLessonsTherapeutic riding
4.9Rating
23Reviews
3Services

Hey there guys, thanks so much for your kindness and friendship and a great opportunity experience for me to have a chance to be able to horseback ride again.

★★★★★ Tonio, Apr 2024

Arrowhead Farm

174 Indian Hill Rd

Trail ridesLessonsBoarding
4.9Rating
23Reviews
7Services

Did a trail ride and had a great time.

From a Google review

Serendipity Stables

230 Jordan Rd

Trail ridesLessonsBoarding
4.6Rating
24Reviews
7Services
Trail rides: per the stable's website

More stables with guided trail rides in Massachusetts, by city

Canton 1 stable

Carver 1 stable

  • Old bear farms53 Main St, Carver · ★ 4.5 (2)
    Trail rides: per the stable's website

Concord 1 stable

  • North Bridge Farm555 Hugh Cargill Rd, Concord · ★ 5 (2)
    Trail rides: per the stable's website

Dartmouth 1 stable

Dudley 1 stable

East Bridgewater 1 stable

  • Pony Town Parties1194 Plymouth St, East Bridgewater · ★ 4.8 (55)

    My wife and I really enjoyed the trail ride at Burrage Pond.

    From a Google review

Groton 1 stable

  • Hazel Grove Park166 Jenkins Rd, Groton · ★ 4.9 (22)
    Trail rides: per the stable's website

Medway 2 stables

  • Next Venture Farm73R Oakland St, Medway · ★ 4.9 (15)
    Trail rides: per the stable's website
  • Saddle Rowe Inc73 Oakland St, Medway · ★ 4 (4)
    Trail rides: per the stable's website

Milton 1 stable

Plympton 1 stable

Randolph 1 stable

  • winsomeriding384 High St rear, Randolph · ★ 5 (12)
    Trail rides: per the stable's website

Rehoboth 1 stable

  • Foxmerle Farm88 Chestnut St, Rehoboth · ★ 5 (4)
    Trail rides: per the stable's website

Rowley 1 stable

  • Silver Shoe Farm183R Haverhill St, Rowley · ★ 5 (3)
    Trail rides: per the stable's website

Sandisfield 1 stable

  • Sunny Rose Farm19 Dodd Rd, Sandisfield · ★ 5 (3)
    Trail rides: per the stable's website

Sterling 1 stable

  • Windstar Farm25 Osgood Rd, Sterling · ★ 5 (4)
    Trail rides: per the stable's website

Upton 1 stable

  • Stone Arbor Farm154 W River St, Upton · ★ 5 (6)

    I went on an organized trail ride there and it was a great time, very well mapped out for our group!

    ★★★★★ Lucy, Oct 2019

Westfield 1 stable

Williamstown 1 stable

  • Clover Hill Farm249 Adams Rd, Williamstown · ★ 5 (33)
    Trail rides: per the stable's website

Before you ride

  1. Wear long pants and boots with a small heel. Jeans stop the saddle rubbing your legs, and a heel keeps your foot from sliding through the stirrup. Sandals and flat sneakers are a poor fit.
  2. Ask about helmets. Many stables lend riding helmets. Ask whether they have one that fits, or bring your own riding helmet.
  3. Ask about rider rules. Each stable sets its own limits on age, weight and riding experience. Ask before you book so nobody in your group is turned away.

How a guided trail ride works →

Trail rides in Massachusetts, by city

The number counts the stables on this page; each city link opens every riding stable we list there.

More in Massachusetts

All riding stables in Massachusetts → · Guided trail rides near you: every state →