How to Plan the Perfect Day Trip

I’ve always enjoyed a good day trip, and in this past year I’ve turned my interest into an art form. For me, a day trip is the perfect way to see new, interesting places, enjoy beautiful sights, and connect with friends or family. Don’t get me wrong, I long for future days of Caribbean and European vacations, as well as long weekends away. But for now, a day trip is an inexpensive way to rejuvenate and have some fun.

I’m going to share my planning strategies and a recent day trip adventure. And in case you don’t enjoy the planning piece of it as much as I do, follow my blog as I’ll continue to share preplanned day trips you can take in the future.

I am lucky enough to live in Massachusetts. There are many things I love about New England, but topping that list is the ability to quickly travel by car to several different states. In addition to MA, I can easily be in Connecticut, Rhode Island, New Hampshire, and even Maine or New York for a longer day trip.

When I decide to plan one of these adventures, I figure out how much time I have for that day, and who my travelling companion will be. My fellow traveler is important as I try to plan activities that I think they would enjoy. For example, if my daughter Bridget is going to join me, I’ll plan to visit thrift or antique stores.

Once I’ve identified my co-pilot, I start to peruse the ongoing lists that I maintain of possible places to visit (for more on my list compulsion see my recent blog “A list for the lists”!) I’ll pick out one or two activities that match my guest, and timeframe for travel, also taking into account seasonal activities and weather. Once I’ve identified that my top activities are feasible for that day, I might google the area or trip advisor to fill in some more possible stops. You might just like to wing it and drive out there and see what ‘s what, but I personally like to have at least 3 ideas of places to stop prior to heading out for a long drive. Honestly, I usually plan more items than we can feasibly accomplish. This allows for surprises–such as rain, or a spot being closed unexpectedly–and it also allows my travelling companion to have some say in what we do. I can show them the list of possibilities and let them select their favorites.

If I’ve found 2 or 3 main activities and I know we’ll have more time to spend, I’ll fill in with some favorite activities by googling the area by topic: Country stores, hikes, and restaurants top this list of possibilities.

Lastly, I print a map (yes, paper!) of the area and mark our potential stops. This gives me a better idea of how much time we’ll need, and also will help me plan the order of activities so we aren’t constantly backtracking because we aren’t sure which activity is closest.

After this, the only thing left to do is pack some snacks and hit the road!

Here’s how a recent day trip went with my 17 year old son, Dylan, during his recent school vacation. Dylan and I had about 5 hours to plan on this day. Rain was predicted late in the day so I knew I would want to schedule any outdoor activities earlier in the morning. As I started to review my list of ideas, I kept in mind that Dylan likes to see unusual things, especially if they might be spooky, and he also loves taking pictures. After running down some ideas, I decided to begin with an abandoned railroad tunnel in Clinton, MA. This offered both photo opportunities and an eerie atmosphere that I thought he would like. Also added to my list was the Wachusett dam and reservoir which looked interesting and appeared to be close to the tunnel. After this, I searched the area for a picturesque hike that would be close by, as I love starting my day in a peaceful environment with pretty surroundings and the opportunity for a little exercise. This search yielded Brewer Brook dam trail, in nearby Berlin, a 1 1/2 mile, relatively easy trail around a small lake. I figured these 3 activities, followed by a nice lunch, would make a great day. I mapped out the locations, filled Dylan in on the plan, and declared a 9:00 a.m. start time.

I was very happily surprised to awaken to a beautiful, sunny day. Since I’m an early riser, I had plenty of time to pack up some snacks and water, as well as making sure I was prepared for rain or mud (on our hike) by packing a sweatshirt, umbrella, and boots. Based on the map I had created, our itinerary looked like this:

1 Hike at Brewer Brook Trail

2 Clinton Rail Tunnel

3 Wachusett dam and reservoir

4 Lunch at restaurant of Dylan’s choice

We left at about 9:15, almost on time! Not bad for a morning trip with a teenager on spring vacation. Our first stop would be the hike, and GPS had us arriving there in about an hour. We had a relaxing drive with minimal traffic and located the parking area for the trail fairly easily. The trail map in the parking area showed an easy loop around a pond, so we set off with our cameras ready. The trail appeared well traveled and well marked. We came quickly to the lake and noticed in the water a teepeed fencelike construction, and when I wondered what it could be, Dylan had already figured out that it was an outlet that the water fell into (photo, above). I had never seen anything like this before but after reading about it after our day was over, I learned that it was for flood control.

As we headed to our left, with the lake on our right, we easily found the trail, marked with orange stripes on the trees, and headed into a more wooded area. It was a narrow path that followed pretty closely to the lake. Dylan was the first to spot a long, tree limb that had fallen to the water and was filled with small turtles sunbathing. As they heard our approach they dropped into the water one by one and by the time I could pull out my phone for a picture, there were only one or two left. It was not much further that we found a sign on a tree describing the beaver lodge. We could see evidence of beavers in the holes surrounding the dam at the lake’s edge, and also saw many chewed branches, further evidence of their presence, but we didn’t actually see any beavers. We continued our path around the lake and Dylan pointed out several black snakes as we walked.

When we came to the end of the lake and were starting to make our right turn to come around the other side, our trail markings suddenly became white instead of the orange we’d been following. We were clearly heading in the right direction, so we continued on the path, with the lake now a somewhat more distant presence on our right. It wasn’t long before we started to see some junk piles in a clearing, and eventually a couple of houses, and it became clear we had veered off the trail. We decided to continue forward, after consulting our phones and seeing that we were close to the road. Eventually we came to a small dirt road and passed several more houses, obviously in someone’s yard, but there was no turning back at this point. Soon we arrived at the main road, and it was a short walk back to the parking area.

This was not my first time getting lost on what seemed like such an easy trail to follow. Despite all of my hiking, my inner sense of direction has not gotten any better. I really wanted to go back and try to find out where we had gone wrong, but we had other things we wanted to see, so we grabbed some water in the car, and got back onto the road. Someday I will go back and find the right path.

Our next stop–the tunnel– was just 10 minutes away, so we found the graffitied stones that marked the tunnel pretty quickly. I could not see the tunnel entrance or any parking, but as we passed the area, Dylan spotted a set of stairs that he suspected led up to the entrance of the tunnel. When we turned around to find a spot to pull over, we saw the Wachusett dam and reservoir almost directly across the street and decided to stop there first. This area had some street parking and was more heavily populated with people. Immediately we could see a great view of the reservoir on the left, with the very steep dam in the middle, and views of the city off to our right. We strolled over to a steep set of stairs leading to the bottom of the dam, taking a lot of pictures as we went along.

We took the steps to the bottom where we wandered through a little park with some trees and a fountain, again taking pictures and stalling a little at the thought of climbing the steep and lengthy staircase back to the top. Eventually we knew we had to get going, so we slowly made our way back to the top. Many people were sitting on the lawn, or the short concrete walls enjoying the views and the beautiful day. We finally made our way back to the car for the short drive back to the tunnel.

We parked on the side of the road and climbed a small embankment where we immediately saw the entrance to the tunnel. Graffiti was plentiful here. There was another couple walking through the tunnel so we paused to take some pictures and Dylan climbed up the side of the tunnel and sat at the top. Once the other couple were out of view, we entered the tunnel where the temperature dropped at least 10 degrees. It was only 2/10 of a mile long and we could see daylight at the other end. Dylan did not really appreciate my joke that we were literally seeing the light at the end of the tunnel.

As we ventured in further it got darker and darker and eventually we needed the flashlights on our phone to see where we were walking. Several areas had leaks and water dripped down, or poured down in a couple of places, and we had to watch out for puddles. As we had anticipated, it was a little spooky walking through the tunnel and I shuddered to think how dark it would be at night. Some people obviously had had that experience as there was quite a bit of trash left in the tunnel. I found myself wishing that anyone who came to enjoy the tunnel would at least clean up after themselves so that others who came after them could enjoy it. We made it to the other end relatively easily and paused to take some more photos before heading back through the tunnel to the opening where we had entered.

Soon we were back in the car and ready and hungry for our final stop: Lunch! I had selected 3 or 4 nearby restaurants based on 3 criterium: Good ratings, good food selection, and a liquor license. Cuz mom gets thirsty after a morning filled with activities.

Dylan selected a place called O’Connors, an Irish Pub in nearby Worcester. As we pulled up we could tell we had picked a winner, as the lot was filled, even at lunchtime on a Wednesday. They had some nice outdoor seating but it had started to rain a bit and we gladly made our way inside, where we waited only a minute before being seated. O’Connors is an old fashioned pub with many little rooms so although there was a lot of seating, we felt like we were in a room to ourselves. Service was prompt and we ordered drinks while continuing to review the lengthy menu. Dylan ordered his usual chicken fingers and I had a “grownup” grilled cheese (cheddar and brie) with a cup of butternut squash bisque. We both thoroughly enjoyed our food and we had great conversation about our day and other things going on in our world.

After a very enjoyable day, it was time to head home. We got a lot in in a short time, combining exercise, interesting sights, good food, and good conversation. Overrall, a very successful day. Oh by the way, total cost for the day: $30, the cost of lunch. It was almost sad knowing the day had come to end. But never fear, plans are already under way for the next exciting day trip!