Best Easy Trad Climbs in the Boston Area


On the skin up Moosilauke’s Carriage Road a few weeks ago, one of our friends was asking about routes in the 5.5-5.6 range in the Greater Boston area that he could lead in preparation for his upcoming AMGA Single Pitch Instructor Assessment. Here’s Part 1 of the list we put together for him, with a little beta for each route.

Black & White Rocks

  • Endgame (5.6) – Fight the temptation to take the easy out halfway up.
  • Twist and Crawl Wall (5.7) – A fun lead with good gear that’s longer than you expect. Consider scouting the anchor beforehand; we remember it being tricky (but that was more than 10 years ago).

Crow Hill

  • Beginners Blessing (5.4) – Good gear and great stances to place it from make this route a blessing for beginning leaders.
  • Layback (5.6) – Like many climbs on this list, we only wish it was longer. Interesting climbing and great gear make it a fun lead, just remember to bring big protection, as it takes up to #3 cams. We even placed a Big Bro on it back in the day.
  • Tom’s Dilemma (5.5+) – Beware of old routes rated with a plus. Many people find this route more in line with 5.7 or 5.8; however, it takes good gear and is easy to top rope, allowing you to unlock the moves and gear placements.
  • The Chimney (5.6) – Two pitches! Dispatch a fun but forgettable first pitch to a large ledge (great for anchor-building practice, but watch out for poison ivy). Pitch 2 brings the goods with an airy exit overlooking the Fisherman’s Wall—home to one of Crow Hill’s hardest climbs.
  • Sidewinder (5.7) – Another Crow Hill sandbag. Gear is a little tricky for the first 20 feet, and so is the climbing, before leading to easier terrain and ample gear. Bolted anchors at the cliff top make this one easy to top rope before committing to the sharp end.
  • Boardwalk (5.5) – Pure joy! This low-angle crack has everything a new leader is looking for: big jugs to hang on while placing gear, nice ledges to stand on for shaking out, and it protects beautifully. The hardest part is getting off the ground and gaining the crack.

Hammond Pond

  • Half & Half (5.4) – A fun, easy lead. If you find it too easy, start in the rightmost crack for a little more straight-up challenge.
  • Pipe Cleaner (5.5) – Another fun, moderate lead. Great practice!
  • Free & Easy (5.4) – The central crack on the face. A number #3 cam is nice for when the crack gets wide at the top.
  • Flutterby (5.6) – Use the cobbles or jam your way up this delightful crack.
  • Crack Jack (5.6) – A stellar finger crack that will make you think you’re at Indian Creek (okay, maybe not) when you’re really just minutes outside of Boston. Beware of the high first piece and watch the ground fall!
  • The Cleft (5.4) – Easy climbing, great gear, and a bailout to your right. A perfect route for getting comfortable on the sharp end.

Quincy Quarries

  • White Knight (5.5) – One of our QQ favorites. Protect the low crux, and have your belayer stand close to the wall to prevent an awkward zippering force on the first piece.
  • Black Knight (5.6) – Great lead, but beware of the marginal protection between the first piece and the roof. Also make sure to extend the cam (Red BD) that you place in the roof, otherwise the rope will get stuck in the crack.
  • Boardwalk (5.4/5.5) – Our first trad lead. Good route for practicing extending gear, managing a short traverse, and thinking about extending the anchor. Not the best protection in the first 10-15 feet.

Rattlesnake Rocks

  • Monday Morning Direct-Direct Start (5.5/5.6) – Starts above the overhanging slab on the right. Traverse the slab left, then climb through a roof (crux) to join Monday Morning Slab. Put this route on repeat to get lots of practice placing gear.
  • White Face (5.5) – A stellar route! Solid gear with steep, consistent climbing. We only wish this one went one for another 1,000 feet.
  • Double Chimney (5.5) – Harder than it looks, especially since we’re pretty sure a hold fell off in the upper chimney a couple of years ago. Use the trees for your anchor.
  • Simple Stuff (5.5) – The bottom is easy, while the top has one move that makes you think. Good protection throughout. Again: use the trees for your anchor.
  • Ship’s Prow (5.7) – Warm up by leading Ship’s Prow Starboard (5.4), then move over to this route. Protects well, even at the crux (which feels hard the first couple of times). Run the rope on a slight diagonal from bottom to top to keep it running smooth.


  • Zipper (5.6) – An awesome flake! The crux comes when the flake (and gear) peters out, so place plenty of protection below.
  • Toejams (5.5) – Obvious climbing and easy-to-place gear should put this route on every beginning leader’s to-do list.
  • Rip Van Winkle (5.10) – Great gear in a 5.5ish crack until there’s no gear and the crack becomes a slab. Smear up the last few unprotected 5.10 moves to the two-bolt anchor.

Looking for more climbing info while waiting for us to finish up Part 2 of our Best Easy Trad Climbs in the Boston Area? Make sure to check out our Trad Climbing Checklist on goEast.


Words by Doug Martland
Photo by Tim Peck


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