There are some sweet roadside attractions to check out! PEZ Candy Museum and Factory photo by Hello Mello via Flickr 

Top Roadside Attractions in Connecticut

1. Gillette Castle - Lyme/East Haddam

A few places around New England feel like the middle ages in jolly olde England. Visiting Gillette Castle feels like stepping into a fairy tale, with this massive stone mansion that looks like a medieval fortress.

2. PEZ Museum - Orange

Few roadside attractions are as sweet as the PEZ Vistiors Center. Fans of the candy (and the fun dispensers) will flip their lids for a trip to this family-friendly–and budget-friendly–spot. A self-guided tour gives visitors a unique perspective on a New England original.

3. Frog Bridge - Willimantic/Windham

Spanning the Willimantic River at South Street, Frog Bridge (Thread City Crossing, officially) features four large frogs adorning the pillars at each corner of the bridge. The statues commemorate a legendary "frog fight" where scores of bullfrogs fought for fresh water.

4. New England Carousel Museum - Bristol

The New England Carousel Museum is a shrine to the artwork and history of the classic amusement ride! The museum has over 33,000 square feet to explore.

5. Hogpen Hill - Woodbury

Hogpen Hill is a 234-acre farm with a serious roadside-attraction sculpture garden. With an RV headed into orbit (Rocket Science 3: Airstream Interplanetary Explorer), a full-scale replica of Stonehenge, and more, this spot will dazzle kids and impress the parents! Admission is charged per car (up to six people).

6. World's Largest Uncle Sam Statue - Danbury

The Danbury Railway Museum is home to the world's largest Uncle Sam statue. This 38-foot statue once stood at the Danbury Fairgrounds, but became a fixture of the Railway Museum–after a hiatus in Lake George, NY!

7. Book Barn - Niantic

The Book Barn is pretty much what it sounds like: a barn full of books. Book lovers of all ages can spend ages browsing through the collection of over half a million books! There are also gardens and animals, including several cats!

 
Some New England roadside attractions are tucked right into the big city! Photo by Scott Edmunds via Flickr 

Best Roadside Attractions Near Boston

8. Hood Milk Bottle - South Boston/Seaport

This enormous milk bottle (over 40 feet in height!) will dazzle kids on their way to the Boston Children's Museum. The milk bottle was originally in Taunton, MA, where it housed an ice cream stand. It was moved to its current location in 1977, and still serves ice cream and other treats. 

9. Museum of Bad Art - Dorchester

Can't get the kids to appreciate fine art at a world class museum? Maybe they would prefer to see bad art at this tribute to the talentless, where admission is free!

10. Original Dunkin' Donuts - Quincy

This one might be less a New England roadside attraction and more of a pilgrimage site for afficionados of Dunkin's world-famous coffee and donuts. This is the Dunkin' that started it all.

11. World's Third-largest Rotating Globe

Babson College in Wellesley, Mass. was home to the world's largest roatating globe until the 1970's. At 28 feet in diameter (and a, uh, earth-shattering 25 tons), the globe is still an impressive sight. Rotating or not.

12. Leaning Tower of Pizza - Saugus

Perched on the southbound side of Route 1 in Saugus, Prince Pizzeria's leaning tower is a local landmark. And the restaurant is perfect for a bite, when the family is on the road exploring New England's roadside attractions!

13. Paper House - Rockport

The original recycler, Ellis Stenman, began building this house in 1922. This amazing attraction is built entirely from newspaper, furniture and all! Admission is very reasonable, only $3 for adults (and $1 for kids). Rockport is also one of the most walkable towns north of Boston to explore with kids. 

14. Dighton Rock - Berkley

This 40-ton rock, located in Dighton Rock Sate Park, is covered with unusual carvings. Many attribute them to indigenous people, but some think the ancient Phoenicians or even Chinese explorers carved the petroglyphs in the 1400s. I think my neighbor Dave did it.

15. Mayflower II - Plymouth

Part hitorical reenacment, part oadside attraction, Mayflower II has the look and feel of the original ship that landed at Plymouth Rock. No trip to Plymouth is complete without checking out the type of vessel that brought the Pilgrims across the Atlantic.

16. Bancroft Tower - Worcester

Another New England roadside castle, Bancroft Tower is a miniature keep, perfect for little explorers. It's located in Salisbury Park, and it's free to visit, a great part of a budget weekend getaway for Boston families.

Top Roaside Attractions in New England - Rhode Island

17. Mr. & Mrs. Potatohead - Hasbro, Pawtucket, RI

Pawtucket is home to Hasbro toys' headquarters, as well as the famous Potatohead couple. Before they were stars in the Toy Story movies, Mr. Potatohead and Mrs. Potatohead were Rhode Island fixtures. And they remain fixtures as giant staues outside Hasbro headquarters.

18. Newport Tower - Newport

Add a visit to this roadside attraction to things to do in Newport, RI with kids. Is this tower a colonial mill or evidence of Vikings in Rhode Island? Either way, it's in a lovely park. And Newport is a great town to visit with kids!

 
 Bangor Maine is home to one of New England's icoinic roadside attractions. Paul Bunyan photo by Amy Meredith via Flickr

Best New England Roadside Attractions: Maine, NH, and Vermont

19. Paul Bunyan Statue - Bangor, Maine

This statue of the legendary lumberjack stands over 30 feet tall, keeping watch over Bass Park in Bangor, Maine. Rumor has it the real Paul Bunyan was just a little bit taller...

20. World's LARGEST Rotating Globe

Completed in 2016, "Eartha" at the Yarmouth DeLorme (Garmin) facility is 41 feet in diamter. Visitors can admire the globe daily until 5:00 pm. It's noticably more impressive (by rotating-globe standards) than the Babson College rotating globe.

21. World's Longest Candy Counter - Littleton, NH

Chutter's in Littleton, New Hampshire is the longest candy counter in the world. 112 feet of glass jars hold an unbelievable selection of sweets (over 500 kinds!) at this candy shop that has to be seen to be believed.

22. America's Stonehenge - Salem, NH

This rock formation has been featured in books and televison shows for decades. The rock formations align with solstices and perhaps represent some kind of temple. Is the site thousands of years old? Is it a colonial comnstruction? Parents can ponder, while kids enjoy the live alpacas.

23. Ben & Jerry's - Waterbury, VT

Apart from the factory tour and flavor-filled ice cream counter, Ben and Jerry's has a "flavor graveyard," where discontinued flavors find eternal rest.