We’ll start in Boston, ride north through Maine, and cross by ferry into Nova Scotia where the roads open up and the pace changes. This ride is about getting out of your routine and into a different way of thinking.

We’ll spend part of each day in focused business conversations, then get out on the road and let the ride do its work.

What we consistently get out of the week is simple.

● We create space to think clearly about our businesses.
● We experience some of the best coastal riding in North America.
● And we build relationships that continue long after the ride ends.

Here’s what to expect:

Before the ride, we’ll connect one-on-one to get you prepared for the discussions. A detailed itinerary will follow.

You’ll also receive packing guidance and ride details so you can be ready from day one.

Sunday 8/9:

Arrival EagleRider, Boston.

We gather and check out our bikes as a group, then we roll our way into Bangor Maine for the
first night.

Hotel: TBD

Arrival Date: 8/9/2026

Departure Date: 8/14/2026

Cut-off Date: 7/9/2026

Day One:

Sunday 8/9: Ride up to Bangor Maine

Easy first day; arrival in Boston, bike pickup at EagleRider, followed by a scenic ride north to Bangor, Maine. We’ll settle in for the evening and prepare for the ride to come.

Day Two:

We’re only a short ride to Bar Harbor and onto the Ferry to Nova Scotia! We then disembark and roll onto our hotel for the night.

Day Three:

Day Four:

After exploring more of Nova Scotia, we leave for a night in Saint John New Brunswick, considered the most Irish city in Canada. The roads leading into Saint John are just as much a part of the experience as the city itself. The Fundy Trail Parkway and the coastal routes offer some of the most dramatic riding scenery in Canada.

Day Five:

We continue our trek back to Boston leaving Saint John and riding into Portland Maine where we’ll enjoy our traditional last dinner together.

Day Six (back to Eagle Rider):

It’s getaway day and we take one last 2-hour ride into Boston returning the bikes to EagleRider before departing for home having experienced another one-of-a-kind CEO Ride.