Plan the Perfect Trail Ride: In Eight Easy Steps

The stars don’t have to be in perfect alignment for the successful organization of a moderate gathering of riders.

Do you want to organize a trail ride, but don’t know where to start? It may not be as difficult as you think. With just a little organization and a bit of drive, you, too, can organize a great trail ride if you keep the following steps in mind while planning your next day outing. These eight steps are all you really need.

STEP 1. Choose a Date

When planning any outdoor activity, including trail rides, weather conditions have to be factored in. Keep an eye on the extended forecast and plan accordingly. Imperfect weather conditions, that can be less than ideal for riding, are likely for each and every New England season. A spring ride would be uncomfortable if downpours were forecast, just as temperatures falling below thirty degrees would chill riders’ enthusiasm for a winter outing. Being aware of predicted weather conditions doesn’t guarantee that the weather will remain perfect, though; it’s best to pack for unexpected weather conditions, just in case.

When selecting a date for your ride, be sure to provide a reasonable amount of notice. Schedules tend to book quickly, so notify riders of the ride at least a week in advance. The option of a secondary date is always a smart idea, especially for any invited fair weather riders. Also, be sure that the ride date doesn’t conflict with other local horse-related events.

STEP 2. Pick a Location

Do you have a favorite place to ride that your friends have yet to discover? Wouldn’t it be exciting to introduce riders to an area that was previously unknown to them? That may be a great spot to host your day ride. If it’s a new destination, confirm that the location is within reasonable trailering distance.

Factor in the seasons when choosing the riding location. Be sure that the parking areas and trails don’t become mud bogs or flood in the spring. If it is an area with low brush growth and few shade trees, opt to ride there during the cooler seasons. Winter may not be the best time to climb a steep mountain trail, due to dangerous footing, but fall may be perfect, and in addition may provide a magnificent foliage view.

Is the terrain conducive to the condition of the horses that will be in attendance? Gentler landscape would be wise in the spring after a winter of reduced work, while long fire road stretches can be ideal for long spurts of cantering later on in the riding season, when your horse is fit for such activity.

As always, seek permission beforehand if you are traveling on privately owned land. Be sure to confirm restrictions on public trail systems. At times, limited use can be enforced due to seasonal conditions or maintenance work. Some state parks request the completion of a day-use permit for larger groups. It’s a good idea to consult park and recreational agencies for any and all day use requirements.

STEP 3. Route

Once you have chosen the ride location, determine the length of the route. Does the trail system offer loop options or will the route backtrack to return to the original trail head? Both types are suitable, it just depends on your personal preference. A route ranging from five to twenty miles is reasonable for a day excursion. Accurately estimate the total distance of the ride so riders know what to expect and how long they will be riding. Be sure to consult up-to-date maps to finalize the route.

Another day trip option is to get dropped off at a location and ride trails or an abandoned rail road bed system back home. Just be sure to calculate the ride time accurately so you aren’t still riding towards home in the dark.


STEP 4. Theme

Just riding with friends for a day is great, but an outing can be even better when a theme is added. Consider packing picnic lunches that can be enjoyed at the half-way point of the ride. Ask riders to bring their pruning clippers for an early spring trail clearing ride. Before the beaches restrict equestrians, plan to visit the sandy shores of a New England beach that welcomes riders for a different type of beach trip. Use your imagination to put a creative twist on the typical trail ride.

Themes can relate to not only what you do or where you ride, but whom you invite. Plan a girls only, or guys only adventure or a mother/daughter ride or even a neighborhood barn outing. Consider making your ride a tradition where the same riders meet each month or at least on an annual basis. In order to minimize the burden of planning, rotate who hosts each ride.

STEP 5. You’re Invited

Unlike the typical invitation to a cookware or jewelry demonstration, people should be eager to participate in a planned ride. Decide how many riders you wish to invite. Groups any larger than ten can become slightly harder to manage, so keep this in mind. Parking at the trail head must also be considered when calculating how many trailers can be accommodated. Do the majority of horses attending travel at the same pace? Are riding styles similar among riders? Do the riders get along with one another? How well do the horses get along with each other? Attempt to gather both people and horses who mesh in order to keep the ride enjoyable for everyone.

Word of the ride can be spread by a call, an email, or a simple note. Announce the date, time, meeting location, and ride details. Be sure to ask invitees to RSVP so you know who is able to come and who won’t be able to make it the day of the ride.


Step 6. Pack Up

For those of you who travel with your horse on a regular basis, you should have the packing list down pat. For equestrians that don’t do it often, it may be wise to review the list of basics. Before setting off on a day ride, be sure to load the trailer with the following necessities:

For the horse: all riding tack, extra halter, lead ropes, grooming kit, first aid kit, buckets, enough water for drinking and bathing, hay nets with plenty of hay, pitchfork, and registration/coggins paperwork.

For the rider: extra riding attire, helmet, sun block, sunglasses, chaps, crop, spurs, hoof pick, multi-purpose tool, pocket flashlight, cell phone, snacks, lunch, water, bag for trash, first aid kit, and emergency contact information.

For navigating: GPS, Compass, road atlas, and trail maps.

Step 7. Travel Time

The trailer and tow rig should have a safety check before the morning of the ride. Inspect vehicle and trailer air pressure, gasoline, oil, radiator, and washer fluid levels. Check the third brake and trailer hook up, along with the connection for the trailer brake lights and turn signals before setting off.

To protect your horse’s lower legs, fasten shipping boots prior to loading. Ensure that their hay bins are filled to help keep them occupied during the road trip. Upon arriving at the trail head, park in consideration of other trailers and vehicles that need to use the area.

Step 8. Ride Out

While waiting for the others to arrive, take this opportunity to unload your horse and have him settle into the new surroundings. By the time he is groomed and tacked up, he should feel relatively comfortable with the new setting. Once everyone else arrives, you should be ready to calmly set off on your ride.

Your Future

After reading this article, planning and achievement of a successful day trip are inevitable! Be sure to pack your horse and a few friends; you will need both for the fun riding adventures in your near future!


Beth, along with her husband and son, lives on a farm in Southern New Hampshire. She is a Bay State Trail Riders member, Barre Riding and Driving Club member and former Director of the Waters Farm Trail Ride Weekend event. Trail riding in the great outdoors serves to renew her spirit and nourish her soul.

If you would like to suggest a trail related subject or pose a question, please email it to with TRAIL TALK noted in the memo line. We look forward to hearing from you!

Categories: Feature Articles