Inside: Sugarloaf Mountain Maryland is a great place to hike, have a picnic with the family, and take a few family photos.

When most of us think of traveling we think of sandy beaches and far away tourist spots (like our upcoming family trip to Singapore). But family travel doesn’t always have to be to far off destinations. Our family loves taking day or weekend trips to explore the nearby world around us.

Call it a staycation or, like we prefer, local travel, these types of smaller trips are great bonding experiences for the family. Plus they are a low cost alternative to satisfy our wanderlust between larger vacations.

I’m always on the lookout for new places for us to explore–extra points if said place can be explored for free. That’s how I came across Sugarloaf Mountain in Urbana, Maryland.

Sugarloaf Mountain is a privately owned park that is free to the public. It has several trails that vary in length and difficulty. And it also has a gorgeous wedding venue called Stronghold mansion. Since I am always on the hunt for new and beautiful places to take family pictures, I jumped at the chance to knock out two birds with one stone.

Sugarloaf Mountain is a couple of hours away from our house but close enough to make it a day trip. We were going to be gone for most of the day I made sure to pack plenty of food and snacks for the trip.

We had some pre-packed trail mix on hand so we packed some of those. I made some delicious pesto, arugula, and onion wraps. Then I filled our spread out with some fresh fruit: grapes, oranges, and strawberries. I prepacked our food using our new favorite meal prep containers.

This was our second hike with Reeves so of course we had to plan around having a toddler in tow. We brought our rugged stroller in the hopes that the trails would be navigable by stroller. Reeves has always been a big baby and that hasn’t changed much now that he’s creeping closer to two years old. He is an excellent walker but hiking on uneven surfaces is a completely different story. We also packed our Ergo 360 baby carrier in case our stroller couldn’t handle the trip.

The morning of the trip, we ate breakfast then hit the road.

When we got to the mountain, the first thing we did was head to Strong Mansion to try to take our family photos. Unfortunately, they turned us away. It turned out that not every part of the mountain was open to the public. Still, I managed to snap this picture of Alexis before we left.

I love multitasking like this. It takes a lot of work to mobilize the family and get us out and about. It makes perfect sense to try to combine multiple to-dos when you can. I love taking family photos a few times a year. All it took to turn this family hike into a photo shoot op was to bring a change of clothing or two and our camera gear. You can check out my tutorial on how we take our own family portraits here.

We found a few other places to take photos at the base of the mountain so we didn’t leave empty handed.

After we finished taking our photos, we changed into hiking gear and headed up to climb Sugar Loaf Mountain. On the advice of some fellow hikers on their way down, we left the stroller behind and put Reeves in the carrier. We will be doing a longer review of the Ergo 360 in a future post. We love the Ergo but it may not be the best option for hiking with a heavy toddler.

To save time, we drove up to the first lookout area which is probably about halfway up the mountain. I’m really glad that we did because though the roads leading up to the lookout were paved, they were also single-lane and very narrow. That didn’t leave much room for people (or strollers) when cars drove by.

The lookout area had tables and benches plus this gorgeous view. We stopped there for lunch.

Reeves, in true toddler fashion, was not interested in anything that we packed except for the fruit. Lesson learned here: when hiking with toddler, pack a variety of options. You never know what your picky tyke will want to eat when you are out in the middle of nowhere. In hindsight, I wish I had packed a few baby food pouches (which he LOVES) and some crackers and cheese.

With our bellies full, we headed off to the hike.

There are two trails near the east overlook. The orange trail is a steep quarter mile hike up to the summit. We would definitely have tackled it if we were sans toddler. But since we had a little one, we opted for the longer, but still challenging, white trail. The hike to the summit took us about forty minutes. That includes a 10 minute detour for Joseph and I to swap Reeves and let him walk around a bit.

I have only ever hiked in sneakers. I’m a city girl so my hiking mostly consisted of climbing the stairs of the New York City subway. Joseph once tried to get me to buy hiking shoes and I scoffed, thinking that hiking shoes were kind of gimmicky. Well I learned first hand on Sugar Loaf Mountain that sneakers just do not provide the kind of support that your feet and ankles need when traversing very uneven rocky surfaces.

The view from the summit was gorgeous and well worth the hike. After spending some time admiring the view and catching our breath, we headed back down the way that we came. The walk back only took 20 minutes.

Hiking Sugarloaf Mountain was a great way to spend the day. We’d also planned to stop at Sugarloaf Winery on the way home but we were all pretty tuckered out after the hike. I guess that gives us an excuse to drive back out there and try a few more trails!