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Make Friends in Boston by Making Easy Hikes

Whether you’re an outdoorsy person or not, you don’t have a choice, because you’re a New Englander. That means you’re up to your boots in four seasons of weather with hundreds of places to hike around the Boston area. Learn how sparking an easy hike is a great way to make friends whether you’re new to the area or have been here a long time.

What is hiking in the Boston area like?

Hiking means a lot of things to different people, but when we say the Boston area in this piece, we don’t mean the White Mountains of New Hampshire or Green Mountains of Vermont. There are easy hikes in those regions, but we’re focusing on local places that don’t require a lot of travel or logistics.

So, with that said, hiking in the Boston area can have some rocky terrain, hills, forested paths, and a few bugs to sprinkle in. Unless there’s an incredible amount of ice, you will be able to hike all year throughout Boston without special gear.

Now that we’ve defined local hiking conditions, you have to choose a place.

A group of adventurers at Middlesex Falls, a close reservation to Boston. Start as strangers — end as friends!

Step 1: Find a local place to hike

People have been posting easy hikes on since 2016, and our data says that hikes under an hour driving distance tend to have the highest participation. We made a list of places you can hike locally to make new friends below that follow the same standard: under one hour of driving.

No car? No problem — you can still post a hike on Ridj-it without a car and get someone to give you a ride by sparking an easy hike. We’ve had non-drivers posting hikes on Ridj-it for 8 years, because you shouldn’t need a car to go hiking. Boston Magazine wrote about our carpool tool if you want to take a read.

Local places to hike

  • Blue Hills

  • Middlesex Fells

  • Breakheart Reservation

  • Harold Parker State Forest

  • Whitney & Thayer Woods

  • Maudslay State Park

  • Appleton Farms

  • Great Brook Farm State Park

  • Halibut Point State Park

  • Crane Beach Dunes

  • Mine Falls Park

  • Assabet River National Wildlife Refuge

  • World’s End

  • Ward Reservation

  • Rock Meadow Conservation Area

  • Whipple Hill Conservation Area

  • Arlington Great Meadows

  • Mary Cummings Park

Want more ideas of other places you can hike? You can go to, and once you have an account, click “Post your trip” and then “Search past adventures” to see a record of other hikes trip sparks have posted throughout New England.

Step 2: Choose a trail

Relax — You’re not going to get so lost that you won’t be able to make it back to civilization. That’s why we’re recommending easy Boston-area hikes.

There are several ways to choose a trail.

  1. Download AllTrails or Gaia GPS; they’ll have pre-loaded trails you can choose from with reviews.

  2. Google the name of the property and then add the word “map” afterwards. Yup — that simple.

  3. Stick with 3 – 5 miles for an easy hike, but you can extend it if the group is feeling saucy once you’re out on the trail. Yes, elevation gain can affect how hard or easy a hike is, but because we’re sticking locally, let’s not fret over that too much right now.

A hike that was posted to Whitney & Thayer Woods. Some people got there by carpooling, and others met at the trailhead.

Step 3: Find a place to eat or drink at afterwards

Hiking makes you hungry not just for food but for a cozy and fun debrief after being on the trail. Have a few places in mind to go afterwards to solidify those friendships, and make sure to write them in your trip description.

Step 4: Let everyone know what gear they’ll need

Truly, and we promise, choosing the right gear for a local Boston hike is not rocket science. Again, you’re not going to the White Mountains, so if the weather looks cold, tell folks to bring hats, non-cotton clothing (including socks), gloves, etc.. Hot? Sunglasses, a hat, and plenty of water.

However, if the trails are very icy, consider investing in a pair of microspikes. You can read more about microspikes versus crampons on this link.

Step 5: Post your event

Hey, you’re reading an article on our blog, so surprise, surprise, we would love to have you post an event on Ridj-it.

But how does posting your easy hike on Ridj-it benefit you? We’ve been around since 2016, and Ridj-it draws a lot of folks who want to make friends and experience the outdoors. We’ve had hundreds of adventures posted on Ridj-it, and over 7,000 carpool rides have been hosted on the platform. (Even the Boston Globe wrote about how we help folks get outdoors together ). People who’ve used Ridj-it have made life-long friends and have even gotten married. Heck, there are probably Ridj-it babies at this point, but note, we’re not a dating platform, so don’t be weird.

We really, really love helping people connect to each other and the outdoors, so when you post an event on Ridj-it, we’ll broadcast it to our other channels around Boston. You can also post the Ridj-it link on other social Boston groups you might belong to.

Posting on Ridj-it is easy. Just have your trip description ready, or recycle someone else’s from the past trip search.


Are there any specific trails in the listed local hiking places that are particularly popular or recommended?

Blue Hills and Middlesex Fells are the most popular and have lots of people all year. These two are the closest and easiest spots with plenty of trails to choose from.

How safe is it to get a ride from a stranger on Ridj-it? Are there any safety measures in place?

Every driver has to upload a valid driver’s license in order to drive, but the question you should be asking as well is, “How safe is it for drivers to give rides to strangers?” Ridj-it is not a rideshare service; we’re a place where you can post an adventure and use our tools to help more people join. The carpool tool is one that people use the most, and the more people in your car, the less likely there are bad actors. We’ve been doing this for eight years with over 7,000+ rides, and we have the data to back that up. You can also make sure “guest signup” isn’t activated which forces people to create full profiles. We reject shady-looking profiles.

Spark a hike to Blue Hills, one of the largest tracts of land near Boston.

Are there any fees or costs associated with using Ridj-it to organize or join hikes?

There are several ways to join a trip: rider, driver, or non-carpooler. Riders pay a carpool fee, drivers pay a fully-refundable deposit which they get back after driving plus get comped for gas/wear and tear, and non-carpoolers pay nothing.

However, some people post charity hikes and require everyone to pay a ticketed fee to join to help fundraise. That’s up to you, and we just provide the tools to make that happen.

Can I have people use the carpool tool for free?

No, but you can always disable the carpool option and then go ham on the comment wall trying to figure rides out. However, let’s say you’re doing the Freedom Trail in Boston: that doesn’t require carpool at all, so you wouldn’t want it anyways.

How can I ensure that the hike I choose is suitable for beginners or those with limited hiking experience?

Read the reviews from apps like AllTrails and Gaia GPS. Those users have crowd-sourced lots of good data.

Can I bring pets, such as dogs, on these hikes? Are there any specific trails that are pet-friendly?

Trip sparks have the option of enabling or disabling dog-friendly hikes on the Ridj-it platform. You should research if trails are dog-friendly or not before sparking or joining a hike.

How do the seasons affect hiking in Boston? Are there any particular times of the year that are best or worst for hiking?

Every month is a good month for hiking in the Boston area — it’s just a question of what gear you have to make sure you’re comfortable. Do your research and don’t be afraid to spend some money. Being able to enjoy the outdoors anytime you want without suffering from the elements will make you feel invincible, and the bonus is that you can wear the same gear around town whether you’re on Newbury Street or Comm Ave.

How long does it usually take for a hike to get participants after it's posted on Ridj-it?

Depends — if you spark an adventure three days before the hike begins, you might get nobody. If you spark the hike with two weeks of wiggle room, you might get 20+ interested people. Posting with as much time as possible is best.

What if someone unwanted signs up for my hike?

Just shoot us an email saying you want the person removed:

Can I use Ridj-it for organizing other outdoor activities apart from hiking?

Absolutely! We’ve had people organize bike rides, ski trips, and more.


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