Middlesex Fells Reservation: A Picturesque Hiking Oasis Near Boston
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Middlesex Fells is a beautiful natural recreation oasis ideally located just a short drive from Boston. It’s a quick daytrip for anyone who wants to get away from the city congestion for a few hours. The reservation is located in the towns of Winchester, Stoneham, Medford, Melrose, and Malden. Walking amongst the beautiful forests, you will feel as if you took a 3 hour drive up to New Hampshire or Vermont, although you never left the state.
It’s the perfect nature escape for those who live in the hectic, congested city and suburbs. Mike and I usually are out and about in the city enjoying historical attractions most weekends, but we also love exploring the many quiet parks and hiking areas throughout the metro. I really love that you can enjoy a mix of both big city and natural attractions in the same region. Since moving to Fall River, I have had a great time mixing various urban and rustic activities.
Anytime we need an escape, we know that the metro has an awesome park where we can soak in some nature for a bit. Middlesex is one of just many large recreational areas within close proximity to the city. The highlight of this particular hiking area is the variety of trails and amazing views of the city skyline.
Year-round seasonal fun
With 100 miles of multi-use trails, there is something here for everyone! Trails are open year-round for hiking, biking, running, and cross country skiing (when there is enough snow). Hikes range from easy to advanced, so everyone can find something to suit their current fitness level.
Trails are separated according to area: West of Route 93 and East of Route 93. We chose to hike the Skyline trail on our first visit. I would love to come back to enjoy some leaf peeping and maybe even cross country skiing in the near future.
The Skyline Trail
We were on the western side in Medford, so we chose to embark on the Skyline Trail, a 7 mile moderately difficult trail with plenty of uphill and downhill climbs. This entire trek will take approximately 5 hours, more or less, depending on how many breaks and pictures you decide to take.
It’s definitely a workout and a trail you need to be in pretty good shape to complete in full. If you are not up for a big challenge, I recommend picking one of the easier treks like the Long Pond Nature nature trail which is just a mile and will only take about an hour.
No matter which trail you decide to go with, it’s a beautiful place to get lost in nature – I really love the secluded wooded scenery. While we see similar scenery at most parks in the region, this place felt surprisingly tranquil despite being so close to the city. I enjoyed the many streams along the way. It was a hard workout, but a really scenic journey, so worth it in my opinion.




Fabulous views of the cityscape
The highlight here is the incredible viewpoint of the city skyline. It’s one of the best places to obtain a full, unobstructed view besides Bunker Hill along the Freedom Trail. While I wouldn’t say that Boston is home to the skyline in the country, the view here is about as good as it gets.
There are numerous places in the metro where you can hike to a city view including Blue Hills Reservation, another popular hiking area with a similar Skyline Trail. In my opinion, the view here is even more fantastic, so if city views is what you are after I would go with Middlesex. On the other hand, Blue Hills is even more rustic with a wider range of trails, so this is one of my top hiking picks overall near the city.
Note: the Skyline Trail is only open to hikers, however, the adjoining Reservoir and Mountain Bike Trail are multi-use paths.

Best time to hike
For our hike, it was a beautiful 60 degree day, the perfect hiking weather in my opinion. Plenty of hikers, dog walkers, and bikers were out enjoying the spring conditions. If only the trees had their leaves again! I imagine this hike would be spectacular during fall foliage season.
While I would like to say I will be back again, there are so many different parks and preserves I want to get around to visiting while I am in such close proximity. I would love to come back here for a leaf peeping or cross country skiing adventure if I can fit it in somehow.
Whether you are a local or a tourist, it’s great to get out into nature after being cooped up indoors all winter. Hiking the Skyline trail was an invigorating workout, but at the same time, a rejuvenating and rewarding experience.
Check out the Trail map to plan your route.
Parking: We parked in Medford on South Border Road. There are plenty of free spaces along the road. Note: I didn’t see any bathrooms or water fountains. Make sure to bring plenty of water with you if completing the Skyline trail – it’s an intense workout! Note that leased dogs are allowed (4 per person).