Favorite Hill Climb Loops

Here we have begun compiling a library of great climbing rides. Several of the rides offer over 10,000 feet of climbing in 100 miles. Low traffic back roads and great scenery are the norms. Expect to suffer at least a little.

A few of the rides entail seasonal gravel sections (closed in winter) and may not be suitable for everybody. These sections will be described in detail in each report.

The capstone of all climbing rides in the northeastern part of the country is the Six Gaps of Vermont loop. Per TopoUSA, it punishes those strong enough to complete it with 14,500 feet of climbing in 132 miles. 6-Gaps also contains the steepest paved mile known in the northeast, the east side of Lincoln Gap which averages 20-24% grade for the last mile.

Mt Greylock/Petersburg Pass: A nice loop I’ve done multiple times straddles the border of MA/NY, which roughly lies on the Taconic Crest mountain range (great mountain biking by the way).

The ride starts in North Adams, climbs over Mt. Greylock, and continues west into NY, coming back over Petersburg Pass. There’s a third climb along the way adding hundreds of additional feet of climbing.  Altogether, the ride runs about 62 miles and 5000+ feet of climbing.

The details: Park at Heritage State Park in N. Adams, MA. Climb Mt. Greylock from the north as described on the mountain climbs page. Descend Greylock on the south side, taking a right on Rt 7. Take a left almost right away on Bailey Rd.

You will climb almost 500 feet on this road at a moderately steep grade. Turn left on Brodie Mountain Rd, and left again on Rt 43. Enjoy the brief descent. Continue over the state line into NY.

There’s a conveniently placed gas station/grocery store/deli on Rt 43 just before you get to Rt 22 in case you need to refuel. Turn right on Rt 22, heading north for what will seem like forever. When you get to Petersburg, turn right on Rt 2. After a small descent, you will begin climbing in earnest up to Petersburg Pass. The descent down the other side back into Williamstown, MA feels so good. Stay on Rt 2 back to North Adams to your car.

Deerfield Dirt Road Randonnee (D2R2): This ride changes somewhat from year to year, but this ride is actually more difficult than the 6-Gaps of Vermont ride due to most of the roads being unpaved. Expect to ride over 110 miles with around 15,000ft of climbing. The climbs are steep, the gravel can be loose and dry or soft and muddy depending on the weather. See also: North Dakota Bike Trails just in case that’ll be where you’ll spend the summer.

Some of the roads are essentially two-tracks or jeep roads. Cyclocross and mountain bikes are common on this ride. I used a road bike with 28mm road tires. I would not recommend skinnier. The organized start is very early, as most riders will need all available daylight to finish it. In some years, awesome food was served after the ride.

Green Mountains of Vermont – 6-Gaps of VT: Nestled in the heart of the Green Mountains of Vermont is a cluster of mountain pass roads. The area lies just north of Rutland and Killington and all but a few miles of this ride is paved. Six-gaps is perhaps one of the hardest one-day rides a fit cyclist can tackle in New England.

It entails 132 miles over six major mountain pass climbs totaling upwards of 14,500 feet of climbing. Mountain weather and gravel conditions are wild cards to deal with. This ride has become very popular in recent years with many small groups making annual pilgrimages to the Green Mountains.

Ascutney/Okemo Loop: A nice loop with two monster climbs can be put together in central Vermont. The ride starts in Ascutney and passes through Ludlow, climbing both Ascutney and Okemo (aka Mt Ludlow) mountains along the way. Oh, there’s a 1200 foot pass climb on Tyson Road too. Altogether, the basic ride runs about 61 miles and 8,800 feet of climbing, most of it very steep.

We’ve been doing variants of this ride lately, adding an additional dirt road climb or wrapping around Okemo before coming into Ludlow. You can increase the ride to 87 miles with 11,700ft of climbing, or even 94 miles with 13,000ft of climbing, with these options.

Jay Peak/Smugglers Notch Loop: This takes place in the very northern reaches of Vermont, nearly touching the Canadian border. It entails about 12,800 feet of climbing in 115 miles. Most of the roads are very low traffic and provide classic Vermont countryside scenery. One of the climbs/descents is gravel, so keep this in mind when planning this ride. Rain or extended dry spells can make skinny tires on gravel unpleasant.

The best time to ride gravel roads is a day or two after it rains or during parts of the year when rain is more frequent. Because there are many smaller climbs that you can power over in this ride, you will be pretty worn out by the time you reach Smugglers Notch, the final biggest climb. The descent back to Stowe is heavenly.

White Mountains of New Hampshire: I have done multiple variants of a couple of rides in the Whites. I call these White Mountains West and White Mountains East. The rides have Bear Notch in common. The west loop runs 112 miles with 10,500ft of climbing.

It starts in Lincoln, NH, loops over Gonzo Pass, North and South Rd (dirt mountain pass), Agassiz Mtn, Crawford Notch, Bear Notch, and back to Lincoln over the famed Kancamagus Pass.

Variants of this loop can include Sugar Hill near Franconia or Franconia Notch via Rt 18. I plan to add info on a popular loop called 4NaaP – Four Notches and a Pass in the future. See also this comparison of Hillclimb Races for Cyclists.

4NaaP includes Kinsman, Franconia, Crawford, Bear notches, then finishes with Kancamagus Pass. The White Mountains East loop runs about 115 miles with 10,000ft of climbing.

It starts in Conway, NH, goes over Hurricane Mtn Rd, Evans Notch in Maine, Jefferson Notch (dirt to 3000ft elevation), Crawford Notch, and Bear Notch all the way back to Conway. See comments on the Jay Peak ride above regarding gravel sections. Jefferson Notch Road is seasonal and may not open until late spring.

Catskills of New York: A group of us from southern New Hampshire and eastern Massachusetts hit the Catskills for the first time in 2017. Riding there was such a treat, we plan to go back for more. The ride reported here is just one possible route, and we’ll likely do something different and more localized the next time we go back.

Expect most of the roads to be low traffic. Expect extremely steep climbs (such as Platte Cove, also known as Devil’s Kitchen, or the even steeper Glade Hill) that rival the steepness found in northern Vermont.

The scenery is good too. Not all roads are low traffic though, and some of the back roads have eroded chip-and-seal surfaces that are unpleasant to ride on with high-pressure skinny road tires.