Trip Summary 9 Days / 8 Nights Avg miles per day: 35-50 Hill profile: Hilly ✔ I'm Interested

We ran a tour of the Berkshires in June, 2019 and again in 2021 and had so much fun! Join us for eight night tour of the Berkshire Mountains in western Massachusetts and southern Vermont.

The Berkshires is a bucolic region where there are small towns and a unique combination of beautiful scenery, a thriving art community, music, dance and theater. Our tour starts in the town of Lenox, home to the Tanglewood Music Festival – the summer home for the Boston Symphony Orchestra. But we will be there in September, after the orchestra crowds leave and the weather begins to cool a bit.  After spending three days in Lenox, we travel north to the town of North Adams and will stay right next to the Massachusetts Museum of Contemporary Art (MASS MoCA), one of the world’s largest modern art museums. In addition to the arts, you will have the opportunity to ride up Mount Greylock, Massachusetts’ highest peak, and visit many parks and waterfalls, historic villages and even the town that inspired Norman Rockwell! We will continue into Vermont and enjoy riding in the Green Mountain State among farmland, quaint villages, and, oh – some hills!

Day 1 Thursday	We will meet in the picturesque town of Lenox, Massachusetts. The town has both a farming history and was the summer residences of the early 20th century’s 0.01%. The riding is lovely, but it isn’t flat. We will do a short ride in the afternoon of roughly 17 miles with about 1100 feet of elevation. We will be staying in a bed and breakfast in town, which is walking distance to the shops and restaurants in town. We plan to enjoy a group dinner in town. Maybe something will be going on at Tanglewood. It’s too early to tell.
Day 2 Friday	At the Norman Rockwell Museum After a sumptuous breakfast, today’s ride will take us to the town of Stockbridge. If the name Stockbridge is familiar to you it might be because that is the town that Norman Rockwell retired to or perhaps it is because that is where Alice’s Restaurant (the Back Room Restaurant) was located in 1966. Either way, you will have the opportunity to explore the Norman Rockwell Museum in Stockbridge. Stockbridge is also home to the Berkshire Botanical Garden and Chesterwood, the 19th Century summer residence of sculptor, Daniel Chester French. You can ride anywhere from 30 to 54 miles today. Dinner is on your own with many nice restaurants to choose from that are walking distance from the Inn.
Day 3 Saturday	Another delicious breakfast at the B&B. Today’s ride will take you west of Lenox to small towns, lovely vistas and a stop at the Hancock Shaker Village, a restored village with several guided tours, a cafe and a working farm. You might even get to do yoga with the goats. Shorter routes will be in the 35 mile range while longer routes can range up to 60 miles (or more, upon request). Tonight we will stay again at the Brook Farm Bed and Breakfast. We will enjoy a group dinner in town. We will be keeping an eye out for what shows may be offered at the Tanglewood festival as well as Jacob’s Pillow (dance) and Shakespeare & Company (theatre, Shakespeare and more).
Day 4 Sunday	After yet another great breakfast and moving our cars to a location that we can leave them at for a couple of days, we will head north to the town of North Adams. Along the way we will ride the full 12 mile length of the bucolic (and paved) Ashuwillticook Trail. North Adams is the home of the MASS MoCA, contemporary art museum. Other attractions include Natural Bridge State Park, with its marble arches and a lovely short hike to beautiful waterfalls. We will be staying at the Porches Inn right across from the MASS MoCA Museum. The Porches is a boutique hotel built from converted row houses that previously housed the factory workers who worked in the factory that is now MASS MoCA. We will enjoy a group dinner in town.
Day 5 Monday	Today we will stay in North Adams. You can stay and spend the day at Mass MoCA, or you can ride ride on one of the loop rides offered. You can ride an optional challenge ride up Greylock Mountain (at nearly 3500 feet, the mountain is the tallest in Massachusetts). We will also offer a ride that takes you through the town of Bennington, Vermont. As with the other days, today’s choices will range in mileage and hill climb. Dinner will be on your own, with plenty of choices within walking distance from the hotel.
Day 6 Tuesday	We stay in North Adams another day. We offer loop rides that take up to New York State and into Vermont. Or you can ride to the Clark Art Institute in nearby Williamstown. The Museum is known for its collection of French Impressionist paintings, including works by Monet and Renoir. We will enjoy a group dinner in town.
Day 7 Wednesday	After breakfast at the hotel, we will head north to Arlington, Vermont. Stroll the shops, museums and historical homes and sites in Bennington along the way to Arlington. We will enjoy a group dinner at the Arlington Inn. We will offer a shuttle back to Lenox to collect any cars that you may have left for the week.
Day 8 Thursday	Another day of riding if you want, or you could spend the day relaxing at our Inn or exploring nearby Manchester.  Visit Hildene, the historic family home of Robert Lincoln, Abraham Lincoln’s only surviving child. Satisfy your chocolate cravings at the Chocolatorium in East Arlington. Ride, hike, wander and relax. That is what this trip is about. We will enjoy a group dinner on this, our last night of the tour.
Day 9 Friday	Our tour ends after breakfast. If you have traveled to the tour without driving, we can take you to Bennington where you can rent a car or catch a bus to Albany or Boston.

Some of the Rides Include:

Day & Ride	Miles	Ascent
1 Audubon / Railway Museum Loop	18 miles	1100 ft
2 Stockbridge – Sheffield Loop	56 miles	2900 ft
2 Stockbridge – Great Barrington Loop	30 miles	1700 ft
3 Hancock Shaker / East Chatham Loop	60 miles	4100 ft
3 Hancock Shaker / Queechy Lake Loop	34 miles	2200 ft
4 Lenox to North Adams Long	37 miles	1800 ft
5/6 Greylock Mountain Hill Climb Long	40 miles	3600 ft
5/6 Greylock Mountain Hill Climb Short	20 miles	2900 ft
5/6 Williamstown Bennington Loop	40 miles	2100 ft
5/6 Three State Loop	38 miles	2400 ft
5/6 Natural Bridge State Park	4 miles	350 ft
7 North Adams to the Arlington Inn	36 miles	2100 ft
8 Arlington Loop short	24 miles	1700 ft
8 Arlington Loop long	51 miles	3100 ft

 

This is an eight night trip. We will staying at the Hampton Terrace Inn, the Porches Inn and at the Arlington Inn. 

We limit the size of the tour to a maximum of ten couples.

_____________________________________________

What is included?

• Eight nights lodging (see the hotels/country inns below)
• Eight breakfasts
• Six dinners
• Routes
• Luggage transport
• Transport back to Lenox to retrieve any cars

Note that we do not provide any bicycles. We expect that you have a tandem that is in good working order and that you are able to assemble your bike. If you do not have your own tandem, you can rent a coupled tandem from Mel at Tandems East. If you have a tandem that is not coupled, we recommend that you ship your tandem to Lenox before the tour. BikeFlights or Ship Bikes are possible options. 

What is not included?

• Transportation to Lenox, MA (start point) or from Arlington, VT (end point) except for retrieving cars from Lenox
• Meals, other than those mentioned above
• Alcoholic beverages
• Admissions to points of interest not mentioned above

What is the average mileage per day?

Average mileage is in the 25 to 50 mile range. We believe that there is enough to see so that more miles may prevent you from fully enjoying the culture of the area. That said, we can work with you if you would like to ride more miles. Bear in mind, though, that we will not be providing SAG support, except in an emergency, if you are off the main route.

Where will we be staying?

While this could change, here are the inns that we plan to stay in. We stay at the elegant Hampton Terrace Inn in Lenox for three nights, the “retro-chic” Porches Inn in North Adams for three nights and the quaint Arlington Inn in Vermont for two nights. 

How do we sign up?

✔ I'm Interested