Massachusetts may be known for its colonial history and vibrant cities, but the state also has some impressive mountain ranges tucked away in its inland and western regions. From the rounded peaks of the Berkshires to the rugged ridges of the Holyoke Range, Massachusetts mountains provide plenty of opportunities for hiking, camping, and taking in spectacular views.
Mountains can also inspire some clever riddles! Here are 51 riddles about mountains in Massachusetts along with the answers. See how many you can get right on your own before peeking at the solution. Each riddle provides a hint about a specific Massachusetts mountain peak, range, or geographical feature related to mountains in the state.
Riddles about Mountains in Western Massachusetts
Berkshire Mountains
The Berkshires cover the western portion of Massachusetts and contain several notable mountain peaks and ranges like Mount Greylock, the highest point in the state. Let’s start our riddle journey amongst those rolling Berkshire hills!
- Riddle: I’m the tallest peak in Massachusetts, part of the Berkshires’ high country. Start your hike from North Adams and traverse my trails to reach my 3,489 foot summit. What mountain am I?
- Answer: Mount Greylock
- Riddle: I’m a 2,380 foot mountain known for my views and my cave near the summit named after ice formations, though none exist there now. Look for me in the Taconic mountain range. What Berkshires peak am I?
- Answer: Mount Williams
- Riddle: Find me in Washington and my name will seem familiar to fans of a transcendentalist writer. I’m one of the easiest Berkshire mountains to identify by my bare 1,631 foot summit. What mountain am I named after?
- Answer: Mount Thoreau
- Riddle: I’m best known for my natural marble bridge formation that spans a waterfall cutting through my 2,180 foot slopes. Hikers can view it by ascending my Mount Greylock Trail. Name me if you can!
- Answer: Rattlesnake Mountain
- Riddle: Though less lofty than Greylock or Williams, my 1,706 foot summit still yields outstanding views thanks to my situation on the eastern border of the Berkshires. What peak that’s part of the Taconic Pluton am I?
- Answer: Berlin Mountain
Holyoke Range
Now let’s journey east into the rift valleys created by the Connecticut River to explore riddles inspired by the Holyoke mountain Range of western Massachusetts.
- Riddle: Find me and Mount Norwottuck standing guard over the Connecticut River in Amherst. At 1,106 feet I’m one of the Lower of the Seven Sisters. Who am I?
- Answer: Mount Holyoke
- Riddle: My 1,063 slopes top the most northerly of the Seven Sisters. Forge over my Metacomet-Monadnock trail if you dare! What peak am I?
- Answer: Mount Pomroy
- Riddle: I may be one of the lowest Western Massachusetts mountains, but my 935 foot summit still offers gorgeous Connecticut River panoramas. Find me, the humblest Sister south of the river. What peak am I?
- Answer: Mount Hitchcock
Riddles about Mountains in Central Massachusetts
Massachusetts’ central region contains historic mountain crossing and more riddle-worthy peaks to identify.
- Riddle: Though not terribly tall at 1,633 feet, I’m still an iconic Massachusetts mountain, marked by my stone summit tower memorializing those who gave their lives for freedom. What Revolutionary era landmark am I?
- Answer: Bare Mountain (Site of the War Memorial Tower)
- Riddle: These two towns may share my name, but only one contains my 1,706 foot wooded peak. Trails connect my state reservation to Pittsfield State Forest. Name my mountain if you please!
- Answer: Becket Mountain
- Riddle: I’m not one single summit but a 22 mile ridge running from the Quabbins to Wachusett Mountain. The midstate trail traverses my high point, 1,700 foot Watatic Mountain. What legendary ridge am I?
- Answer: Wapack/Watatic Range
Riddles about Mountains in Eastern Massachusetts
Eastern Massachusetts may be more populated but still holds mountain mysteries left to solve!
- Riddle: Find me in Milton near the Blue Hills and I just barely qualify as a mountain, standing only 640 feet. I’m still part of the Greater Boston trail system. What hillock am I?
- Answer: Pine Tree Hill
- Riddle: I’m a prominent 1,477 foot peak located in the Blue Hills range just south of Boston. For one week every April, I’m considered the weather capital of New England thanks to an important meteorological tradition. What windy summit am I?
- Answer: Great Blue Hill
- Riddle: My summit is home to the transmitters for Boston TV and radio stations. I’m located north of Great Blue Hill at 1,095 feet elevation. Hike my Tilley Trail to earn views of the sensational skyline. Do you know my name?
- Answer: Wachusett Mountain
Riddles about Mountain Ranges in Massachusetts
Can you name these Massachusetts mountain ranges from geographic clues?
- Riddle: Named after an English range, I run southeast from Vermont through western Massachusetts, featuring the state’s highest peak, Mount Greylock. What range am I?
- Answer: The Berkshires
- Riddle: I’m a central Massachusetts mountain chain named for an Algonquin tribe, running from New Ipswich, NH to Princeton, MA. Mount Wachusett comprises my northern section. What historic range am I?
- Answer: The Wapack or Wachusett Range
- Riddle: We’re a southern New England range that extends from Connecticut across central Massachusetts. Our steep western ridges frame the Connecticut River valley. What are we called?
- Answer: The Holyoke Range or Mount Holyoke Range
- Riddle: Located in Boston’s southern suburbs, I’m a small but beloved mountain chain managed by a namesake reservation area. Popular hiking trails lead to my peaks including Great Blue Hill. What hilly range am I?
- Answer: The Blue Hills Range
Riddles about Mountain Reservations, State Parks & Recreation Areas in Massachusetts
Several Massachusetts mountains are set aside in dedicated parks and reservations. Can you name the locales where these peaks rise based on geographical and recreational clues?
- Riddle: I’m an 11,000 acre state park surrounding Mount Greylock. Find me in the northern Berkshires near Adams, Cheshire, and Lanesborough. Mile-long vistas and a war memorial atop the state’s highest peak are just some of my attractions. What park am I?
- Answer: Mount Greylock State Reservation
- Riddle: Established in 1898, I’m a historic Boston park featuring the Blue Hills range as well as Ponkapoag Pond and Houghton Garden. What’s my name?
- Answer: Blue Hills Reservation
- Riddle: Farmington River waters pass through my Connecticut River Valley locale near Mounts Tom and Holyoke. I offer camping, hiking, swimming, and cross country skiing around my two mountains’ slopes. What state park am I?
- Answer: Mount Tom State Reservation
- Riddle: Surrounding central Massachusetts’ Mount Wachusett, I boast 22 miles of hiking and ski trails plus opportunities for camping, fishing, boating and swimming. What state reservation are located at?
- Answer: Wachusett Mountain State Reservation
Riddles about Trails on Massachusetts Mountains
These riddles describe famous trails leading hikers to stunning Massachusetts mountaintops and summits.
- Riddle: I’m an iconic foot trail running the length of the Berkshire’s high country from Mount Greylock to the New York state line. Completed in 1930, my name honors the Berkshire Natural Resource Council founder who first envisioned me. What historic trail am I?
- Answer: The Appalachian Trail
- Riddle: This trail shares its name with New England’s highest peak outside the Presidential Range. Winding over Mount Greylock’s slopes, it connects the Berg Kirch parking area with Adams Mountain Road. Name me if you’re able!
- Answer: Mount Washington Trail
- Riddle: I’m Mount Holyoke’s oldest mountain path, wending 2.5 miles and 1,100 feet to the summit. Steamboat passengers once rode the nearby passenger tramway to climb my slopes. What classic trail am I?
- Answer: The Joseph Allen Skinner State Park Trail
Riddles about Mountain Passes in Massachusetts
These Massachusetts mountains are well known for their mountain passes. Let’s see if you can decipher their identities!
- Riddle: Cutting through Vermont’s Green Mountains and Massachusetts’ Berkshires, this famous pass has linked Boston to Upstate New York since the Revolutionary era. What early American trade route am I?
- Answer: The Mohawk Trail
- Riddle: I’m a winding mountain road traversing the high ridge connecting Mount Greylock and Saddle Ball Mountain. Find me in Adams, MA. What dramatic pass am I called?
- Answer: The Notch
- Riddle: This pioneer footpath crosses the Holyoke Range, traversing Mount Norwottock. Its western terminus is the trustees’ Reservation in Amherst. What historic Holyoke trail am I?
- Answer: The Metacomet-Monadnock Trail
Conclusion
I hope you enjoyed these riddles about Massachusetts mountains! Our Bay State may be small but it packs gorgeous highlands and peaks into its inland western and central regions. Whether hiking Mount Greylock’s preeminent heights, traversing Holyoke Range ridges, or visiting Boston’s beloved Blue Hills, Massachusetts mountains offer everything from lofty vistas to mystical glens to century-old trails and passes.
These riddles provide a fun way to explore some of Massachusetts’ exceptional mountains while testing your geographical and outdoors knowledge. From misty Mount Washington in the Berkshires to the urban outlook atop Great Blue Hill, Massachusetts mountains tell tales of history, nature, recreation and more. Now that you’ve solved these riddles and unlocked their peak identities, it’s time to hit the trails and experience these Massachusetts mountains in person!
