Ceremony Music

We did something very similar - an outdoor ceremony & reception at a state park with a DJ. Talk with the DJ and see if they are familiar with the actual ceremony site. Whether they are or aren't, ask them to schedule a walkthrough with you to discuss the following:
- whether the outdoor site's proximity is close enough to be considered included in the cost or whether they'll charge you extra.

-where they will be able to park their vehicle at the ceremony site on the day.
- your vision for using the site (who will be where?)

- and to search for outlets to hook up equipment. If you're truly going to be in the woods without electricity, discuss how the DJ will power their equipment.

-Check the wifi at the outdoor site and if it's unstable, to have your playlist downloaded on their local drive.

-Assess your speaker & mic needs.
-Discuss a rain plan. If you can, think about a Plan B/inclement weather plan so you don't have to improvise the week of your special day.

As you update your timeline, allot time for the DJ to set up and do a mic check. Only takes a few minutes.

Then get everything you just discussed written into your contract or in an email thread with the DJ and the venue for peace of mind.

We also did photos before the ceremony. You just need to time the photography to start before the first trolley arrives. If you plan to take some of your family photos beforehand, you'll need to ensure they reach the woods before the trolley service begins for the other guests. We had our parents and siblings arrive a half hour before our photo session began, and had chairs and extra appetizers and bottled water waiting for them to help them stay comfortable.

It is still possible that some of your guests will see you before the wedding. It's fine! Just take a deep breath and tell yourself it's their surprise reward for boarding the first trolley!
All the best!

We are also doing something similar- ceremony in 2 different locations, but on the same property. We decided the best solution for us was to hire a string quartet to play at the ceremony- no heavy equipment to haul around and set up, and no need for electrical outlets. The venue will simply need to set up a few extra chairs and the musicians handle the rest.

I did already talk to the DJ and they said it's still covered since it's at the same address and I did ask the venue if they have electricity out in the woods and they said they do. I'll talk with the DJ and see if they can set up for the ceremony and have time to set up for the reception too. I'm not sure how long something like that takes. I hope that we can take pictures before the ceremony, but if not then I'm fine with taking pictures in between also.