Ipswich is one of the most beautiful towns in the state of Massachusetts with expansive beaches, forests, farmland, country estates, and winding rivers as well as gorgeous architecture and history. The Ispwich River Ramble is an enjoyable flat route with a few short hills, one of which allows you to visit the Crane Estate on Castle Hill. One section on State Route 1A can be busy and congested but the rest of the route is on quieter country roads. On this ride you will visit Crane Beach, Castle Hill which features a grand estate and stunning views, ramble through vast salt marshes, tour open farmland, and border a section of the Ipswich River.

This is a strenuous ride that is steep uphill for over 7 miles as you conquer the state’s highest summit, Mount Greylock. This arduous climb is not without reward. The paved roads up to the summit offer beautiful scenery and many observation points along the way and the views from the summit are stunning, including panoramic views stretching 100 miles into six states. The descent is fast and the end of the ride is on gentle roads. These mountain roads can have lots of traffic, especially on holidays and weekends. This area is also very popular for hikers and there are numerous trails that begin on and cross these mountain roads. Caution is advised.

This is an epic journey through central Massachusetts from historic Concord, to peaceful Princeton. At Princeton, you will climb Mount Wachusett. This is the biggest climb on the route and offers spectacular views from the top but the rest of the terrain is very hilly as well. The route is mostly low traffic roads or roads that offer wide shoulders with a few major roads crossing and short sections riding along busy roads with a narrow shoulder. As you ride the quiet, country roads you will also visit several quaint towns and view some beautiful ponds and reservoirs. This ride is based on a ride run annually by the Charles River Wheelmen, called Climb to the Clouds.

The Horse Heaven Hills road biking adventure explores a rural and hilly region where you will see plenty of farmland and woods. The scenery on this bike ride has been touted as some of Connecticut's best, and there are several spots with scenic viewpoints on this adventure. Be apprised that while the ride is marked as a low traffic adventure there is a chance there will be some moderate traffic in the town of Washington.

This is a challenging century ride that involves 5,500-feet of climbing that is mostly all crammed into the first 62 miles of the ride. The Souhegan River Classic is painful but beautiful as it takes you through some of the best cycling roads of northcentral Massachusetts and some through southcentral New Hampshire. Virtually the entire route is on low-traffic back roads with gorgeous scenery of expansive open lands, some water scenes, and quaint little towns.

This road biking adventure runs through some of Connecticut's most beautiful wilderness. Some of the features of this ride are the Housatonic River, Tarradiddle, Barrack Mountain, Camp Freedman Pond, forest views and several other hills and mountain areas. You will ride through remote forest-lands with several tree species on display, including maple, oak, sycamore, beech and hemlock.

This road biking adventure offers a secluded ride through a heavily forested area and features Scituate Reservoir. Most of the ride runs around the reservoir and you will even cross over the water at two places on the lake. Tree species that you will find in the forest that lines the roads include ash, birch, maple, oak and pine. Be apprised that while most of the ride has low traffic roads there may be times or places with moderate traffic.

This loop takes a wandering route through scenic countryside east of Peterborough. Located in the Monadnock area, this ride offers views of Mt Monadnock and passes the occasional pond or marsh. Climbs on this route are generally mild excepting one stout grade beginning at mile thirty-two. There are a couple of miles of dirt road on this outing, but they are generally in good condition.

The Shining Sea Bikeway is a community project which was dedicated in 1975 but there are still sections being added to the path to make it even longer. Right now, this path winds through Falmouth toward the ferry terminal at Woods Hole. This is the only bike path along the Cape and offers spectacular views of the open ocean and Martha’s Vineyard. You will also be rewarded by other scenery on this ride including over 20-acres of woods, ponds, swamps, and marshes as well as birds singing and flying overhead. It is the views and the scenery that makes this ride worthwhile and is hardly a workout due to the lack of elevation gain.

This is a great destination for a leisurely ride along the ocean. You will travel through quiet countryside roads to world-famous mansions. The route follows the coastline for some time with great views over the water and also weaves through some parks and forested areas. You will also get the chance to explore some of the kettle ponds that are typical in the area. This route is flat and easy to cruise along and is especially great off-season when summer traffic has disappeared and you have more room and can avoid the crowd.