Skate Spot Tours – Boston by Skateboard

See historic skate spots and roll through one of the most dynamic cities in America. 

Guided by the founder of (Ben Kerrigan), this innovative tour introduces you to the best the city has to offer for rolling, sliding and grinding while taking in all the sights.  This is a stress-free tour which mixes travel by skateboarding, walking and/or subway trains according to your comfort and conditioning.  It’s a great choice if you are a first-time visitor and enjoy urban skateboarding.

Ben is also an accredited skateboard instructor with nationally-recognized certification, so beginner skateboarders with fundamental skills are welcome*. The tour is also perfect for recreational cruising, penny boarders and longboarders!

Skate the Freedom Trail

Depending on your tour length, we will take you to both of Boston’s official skateparks (located in Hyde Park & East Boston)….or choose from a diverse range of skate spots around the city including:

  • Boston Common
  • Boston Public Garden
  • Freedom Trail
  • Custom House
  • Back Bay
  • Waterfront

Skateboarding Adventure Tours

Tours can be personalized to your interests or fully mapped out in advance by an experienced guide. Personalized adventure tours and popular tracks include the following:

Tour A: Skate Spot Underground (optional track, no extra free)

It’s always a challenge to navigate a new city to locate the best ledges and flat ground.  Without a local guide, the advBoston Skateboarding Tourenture can quickly turn into a frustrating and disorienting waste of precious touring time.  Ben has been skateboarding in downtown Boston for nearly 8 years and is a full-time student at Boston College; he focuses on helping you make the most of your visit.

If you are a more experienced skateboarder comfortable with using bike lanes then this tour track may be for you.   The Boston skateboarding scene is vibrant and growing…we’re home to:

  • nationally-acclaimed landmarks and skateboarding spots
  • legendary elements originally frequented by local skateboard pros like PJ Ladd, Jereme Rogers, Many Santiago, and Andy MacDonald
  • uniquely mixed New England architectural ledges
  • a wide variety of possible elevations, stairs and wide plazas
  • coming soon!  a world class flow concrete park (scheduled to open Fall 2015 – Book Now!)

Tour B:  Boston History (optional track, no extra fee)

If you interested in  the founding of Boston and America, we’d be happy to tailor an visits to major historic sights like Faneuil Hall, Paul Revere’s House, South Meeting House, State House, and more.

Affectionately known as the “Shred Coat Tour” we focus on colonial happenings, sites and figures from 1620 to 1822 (with emphasis on the pre-revolutionary period).  You’ll learn fascinating and fun facts about the American Experience as you traverse The Olde Town and get a solid orientation on the lay of our unique topography.  The number and type of local sites is very flexible.

* Requirements:

  • Rider(s) must demonstrate basic pushing, cruising and stopping skills.
  • Rider(s) must be 13 years old or older
  • Rider(s) must be comfortable skateboarding in the bike lane (Skate Spot Underground track only)
  • Helmet required for riders under 18 years old
  • Signed liability waiver (attached to online booking form – button below)

Though not required, it can be helpful to have an MBTA T-Pass CharlieTicket to conserve energy and get around the city efficiently.


Our standard tour fee is $55 per 90-min. session.  $10 for each additional skateboarder (max tour groups of 4).

Your tour includes:

  • A guided tour by an accredited skateboarder instructor and Boston native, Ben Kerrigan
  • Fascinating local and national historic sites
  • Detailed tour routes with custom waypoints (using Google Maps)
  • Flexible start and finish locations! 

Need equipment?  No problem. Through his partnerships with local skate shops and training services, Ben is able to arrange new and used rigs to your specifications with 24 hours of notice.  You might even like the popular Boston Skate Spot deck which Ben designed.

Please indicate your specific needs in the comment box of our online booking form.

Book Tour