Weekend in New England

Friday July 31 to Sunday August 2, 2026

Bike across Massachusetts and Connecticut along the beautiful Pioneer Valley and Farmington Canal

Direct train connections from NYC make for an easy weekend biking getaway

All inclusive – meals, luggage shuttle and vehicle support provided

A weekend in New England is a quintessential destination to escape the city. And it only takes a weekend to do an epic bike tour across Connecticut and Massachusetts! We make it easy with direct train connections and our all-inclusive package. You can literally leave work on a Friday afternoon, get on a train, ride all day Saturday and Sunday, and be back on a train home Sunday afternoon. Easy. Beautiful. Fun.

A fantastic ride, with many conveniences

This fabulous weekend bike tour focuses on the Pioneer Valley (Massachusetts) and the Farmington Valley Heritage Corridor (Connecticut) and is mostly on rail trails with on-road segments in some places. Each day of the tour is distinct, with something different to see, as you pass through historic town centers that were built along a transportation corridor that has been used for hundreds of years. To see a description of the trail we use, click here.

The tour is set up to allow participants to take the train to and from the ride. Along the way, there are many cultural attractions, historical sites, and conveniences. It’s almost like cycling in Europe for a weekend, but you are much closer to home! And of course, our team is always nearby, setting up great rest stops and providing vehicle support to anyone who needs it.

Click the tabs below for a day-by-day itinerary. The price of the tour is $950 per person if sharing a room, or $1200 per person if you want your own room. A list of what is included (and not included) is shown below the itinerary at the bottom of the page.

TOUR LIMITED TO 10 PEOPLE – TO REGISTER CONTACT: 917-748-1119 OR LUKAS@GOTHAMBIKETOURS.COM

Friday July 31

Dinner and hotel stay in Greenfield, Massachusetts

There are several train options that will get you to Greenfield from NYC or points in Connecticut using the Amtrak Vermonter or the Amtrak Valley Flyer. Click here to see the train schedule. You can arrive in Greenfield at 4:22 p.m., 5:30 p.m. or 10:33 p.m. In all cases we will meet you at the train station and bring you to the hotel. If you are on one of the earlier trains, you have the option to join us for a group dinner.

If you need to drive to the tour, you can park in either New Haven or Meriden and take the train a shorter distance to Greenfield (so that you end the tour at your car).

Saturday, August 1

Greenfield to Westfield: 48 miles – A combination of (beautiful) low traffic roads and rail trails

The ride begins at the hotel (Hampton Inn Greenfield) and uses low traffic roads that are signed as bike routes as you make your way south along the beautiful Pioneer Valley. After a rest stop next to the Connecticut River, the ride transitions to rail trail as you pass through Amherst, Northampton and Easthampton where we have a lunch stop. The final stretch into Westfield is again on low traffic roads with another rest stop, as well as an opportunity for lake swimming 5 miles before the end. (You can also just end with the swimming and we will drive you to the hotel). After checking in (Hampton Inn Westfield) we will have another group dinner.

Sunday August 2

Westfield to New Haven: 48, 55 or 68 mile options. Mostly trail with some on-road segments where there are gaps in the trail.

Once again you depart directly from the hotel, and within minutes you are on a long beautiful stretch of rail trail. Soon you will cross the state line into Connecticut, and then you will have an opportunity to bike across the entire state and end in New Haven, which is a 68 mile ride. If you do this, the ride will end at Union Station in downtown New Haven where there is Metro-North train service back to Grand Central every half hour. Click here for the Metro-North train schedule.

If 68 miles is too long, you can also end at the 48 or 55 mile mark and we will shuttle you to the Meriden train station where you can take the Hartford Line train to New Haven and then transfer to Metro-North. Click here for the Hartford Line Schedule. (Depending on group logistics we may also be able to shuttle you to New Haven).

Tour price: $950 per person if sharing a room, or $1200 per person if you want your own room.

Tour includes:

Hotel and dinner on Friday July 31
Breakfast, lunch, dinner and hotel on Saturday August 1
Breakfast and lunch on Sunday August 2
Vehicle support, baggage carry, rest stops and any needed shuttling throughout the tour
Excellent GPS navigation that includes historical information

Not included in price:

Train fare to and from ride
Bicycle (you can bring your own, or rent one for $125 for the weekend)

A (non-refundable) deposit of $200 is required to hold your space.

Note: group meal opt-outs. This trail has many amenities, including restaurants and places to eat. If you prefer to experience the trail more independently, where you eat meals on your own, you can opt out of group lunches and dinners and we will prorate the cost lower for you.

TOUR LIMITED TO 10 PEOPLE – TO REGISTER CONTACT: 917-748-1119 OR LUKAS@GOTHAMBIKETOURS.COM

Can’t make the tour? Consider a self-guided ride with our expert trip plans and GPS! Click here!

See the gallery below for pictures of our Massachusetts and Connecticut bike tour!