Meet fellow urban hikers and explore one of Boston’s highest hills after dark on a 2.5-mile loop hike from and back to North Station, with an optional postlude at Night Shift Brewing for drinks and food.

Boston is a city of trails…and urban hikers. What better way to meet fellow city explorers than by going on an adventure together during the magic hour? After their inaugural winter run in early 2024, Boston Night Hikes are back! Hosted by Miles Howard (founder and lead organizer of Boston’s Walking City Trail), these free group hikes are a unique way to discover Boston’s rustic beauty while connecting with residents and visitors alike.

On this 2.5-mile hike, we’ll meet next to the MBTA’s North Station in Portal Park at 6pm on Monday, January 28th and you’ll pick up the last segment of the Walking City Trail to explore the Boston Harborwalk and Bunker Hill itself. But our return journey will take us underneath I-93, where lesser-known wonders await. And then you’ll conclude with drinks and grub at Night Shift Brewing at Lovejoy Wharf, which is located a few steps away from North Station.

The hike will take place on paved surfaces, with light climbing and occasional stairs. While hike difficulty is subjective, the distance, terrain, and topography will probably make this one an easier hike.

There’s no signup cost for Boston Night Hikes; though Walking City Trail contributions make our work possible and are enormously appreciated! All you need to do is RSVP via this form and show up. There’s also no group size limit for these hikes. (We’ve had over 30 people on some of these hikes!) So if plans change and you can’t make it, don’t sweat it. There will be more Night Hikes later this winter, and beyond.  You can sign up here! 

This hike will be a snow-or-shine event, unless there’s dangerous weather forecasted for the evening, such as extreme cold, a Nor’easter,  or hypothermia conditions like freezing rain. If that happens, then the hike will be rescheduled for a future date and everyone who has signed up will be notified of the date change by email.

ALSO, if you have a spare headlamp, flashlight, and/or AAA or AA batteries that you would like to donate to the first Walking City Trails gear drive (so that owning a light source isn’t a pre-requisite for participating in a Night Hike), bring it to this hike and you’ll receive a free Walking City Trails sticker!

RSVP by entering your name and email further below, and I’ll see you out there.

NIGHT HIKE FAQs

What supplies should I bring for a night hike? First and foremost, bring a flashlight! We will be hiking in some dark environments without the illumination of streetlights, so having a light source is crucial. I recommend a battery powered handheld flashlight, headlamp, or both. While the flashlight on your phone can help too, the cold weather can knock out phone batteries faster, so I don’t recommend making this your primary lighting.

If you like to hike with trekking poles for stability, I recommend bringing those too! They can be helpful at night.

Clothing-wise, I suggest wearing comfortable insulted walking shoes or boots. For upper/lower body warmth, consider dressing in the classic “three layer system.” First, put on an insulating base layer like thermal tights. Second, add a second intermediary layer for warmth, such as a vest or a fleece. Slide into a jacket with wind resistance, and you’re good to go. (You can always discard and put on layers as needed.) Oh, and wear a warm hat too! Keeping your head warm will help the rest of you stay warm amidst winter conditions.

Will we really be hiking in the dark…? Yes! This hike will begin and end well after sundown.

How can I get to/from the hike? North Station, the meetup point, is serviced by the MBTA Orange and Green Lines, as well as the MBTA’s 4 bus. You can also catch the Wachusett, Lowell, Haverhill, Newburyport, and Rockport lines of the commuter rail from North Station. Free parking around here is pretty much impossible to find, and garages are pricey, so if you’re able to take public transit or use a rideshare service, I recommend doing so! From the Night Shift Brewing Pub taproom, North Station is less than 5 minutes away by foot.

What if I’m running late for the hike? Please leave exta time to get to North Station by 6pm, as we will set off around then. On the morning of the hike, a confirmation email sent out to everyone who signed up will include a map of the route, which you can use to try catching up or intercepting the group if you miss the departure.