If you like to hike, this post is for you! If you have a pup, even better. Because all of these hikes are Elsie approved.
Our summer days almost always start with a hike at one of our favorite spots around the Berkshires. Our pup Elsie loves to run through the woods chasing chipmunks and sniffing everything in sight, so we usually aim for a hike first thing in the morning.
There's no shortage of trails in the area but I thought I'd share the ones we love the most. We rent a place in Stockbridge, so the hikes I've included are in close proximity to the Tanglewood area.
- Steven's Glen is a magical walk through the woods and a great place to let your pup run off-leash. Located up the mountain in West Stockbridge, it takes us roughly 45 minutes to hike to the glen, then up to the viewing point, and back again. This length is great for days when we may be in a hurry and under pressure to get Elsie exercised in under an hour. My nieces and nephew commented that it looks like "Twilight" in there and I totally agree. The landscape is remarkably similar to the Pacific Northwest. Be prepared to get your heart rate up on the way back up! Another reason we love Steven's Glen is that there is a stream where Elsie can cool off and grab a drink. Any hike with water on a hot summer day is a win in our book!
Pro tip: there's no parking lot, just a patch of gravel at the trail head with room for 3-4 cars max. Be sure to leave space for others to park if you're the only one there.
- Kennedy Park is where you'll want to go if you're spending time in Lenox. It's super close to town and has 15 miles of groomed trails. Dogs are allowed off-leash here, but be prepared that you may see horses on the trails. We keep an eye out for horses so that we can call Elsie back to us and leash her up until we pass the horseback riders. There are lots of trails within Kennedy Park, so you can spend as little or as long as you want to meandering through the woods.
- Monument Mountain is in Great Barrington and very popular during the summer. It's a longer hike and the most strenuous of the hikes I'm writing about in this post. Prepare for a workout. Whenever we have guests visiting we try to take them on this hike because of the view at the top. (selfies are obligatory - but be careful!) It's a classic Berkshires hike and not to be missed if you have time. Unfortunately, it can get pretty crowded on the weekends so I'd recommend going earlier in the day or better yet, go when it's raining. On rainy days you're guaranteed to have the place mostly to yourself.
This is the only hike that requires you to pay for entry and parking. It's $5 per car for a day pass* that you need to display inside your car on the dashboard. *There's no fee if you're a member of the Trustees of Reservations.
Pro tip: the top of Monument Mountain can be treacherous so take caution. I recommend putting your dog back on lead as you approach the top and until you've descended a good amount. There are some very steep cliffs!
Olivia's Overlook is best known for it's scenic view overlooking the Stockbridge Bowl. It's also a popular spot for photographs, conversation, or eating a meal al fresco. But back to the hiking... We love to meet up with friends for doggie play dates here. There are plenty of trails and like Kennedy Park, you can do as little or as much as you want. It's our new favorite place!
Pro tip: Be sure to grab a selfie like Elsie and Sniff!
- Water bottles for yourselves and your pup. We like the gulpy water dispenser for Elsie and S'well water bottles for ourselves. The s'well bottles are stainless steel, insulated, and look great. We bought ours at a great local shop in Lenox called Design Menagerie. You can buy one here.
- A bear bell for your dog (or you!) Elsie wears this bear bell on her collar or harness to alert any wildlife in the area of her presence. There are black bears in the Berkshires that we don't want to sneak up on, so the bear bell jingles and makes noise for us. I have friends who wear a bear bell on their running shoes too.
- Good hiking shoes. I never thought I'd get excited about hiking shoes but Oboz are the best! They're waterproof and perfect for casual walks in the woods but also hold their own on more advanced hikes. I bought mine at the Arcadian Shop in Lenox, but you can find them here from Amazon.
- Natural Insect repellent for mosquitos and ticks. As lovely as the Berkshires are in the summer, there are lots of mosquitos in the woods. And of course, we try to prevent lyme disease! Adam did some research on organic tick repellents, so we've been wearing Cedarcide for all of our outdoor adventures. It smells like cedar and we don't feel awful about spraying it on ourselves. We also lather some on Elsie's legs too just as an added measure against ticks. Plus, it's deet-free. You can buy it here.
Happy Hiking! Where are some of your favorite places to hike?