Best Roadside Attractions Near Boston

Roadside attractions are those special sights along the highways and byways of Boston that catch the eye of the passer-by. They are unique, beautiful, strangely odd and usually over-sized things that stand out from the typical scenery and landscape. They make passers-by just have to stop. The Best Roadside Attraction In The Boston Area is another resource to find some entertaining places to visit in and around the city. Check it out before heading out on a road trip.

Reminiscent of Italy's Leaning Tower of Pisa, this roadside attraction is a favorite of several generations who have enjoyed the timeless food at Prince Pizzeria. The Leaning Tower of Pizza is a unique and fun structure on the outside facade of the restaurant but once inside, families have enjoyed dining in the large, traditional, family-style dining room that has been open for business since 1961.

Hood Milk Bottle
Boston Children's Museum
308 Congress St.
Boston, MA 02210
(617) 426-6500
www.bostonchildrensmuseum.org

The 40-foot-tall wooden Hood Milk Bottle stands outside the Boston Children's Museum and weighs 15,000 pounds. It has recently undergone a complete renovation and serves as a great family attraction, right on the wharf outside the museum. The base of the famous Hood Milk Bottle serves as a concession stand for hot dogs, ice cream and soda. If the Hood Milk Bottle was actually filled with milk, it would hold 58,620 gallons.

New England's Biggest Chair
In front of the Helen Mae Sauter Elementary School
130 Elm St.
Gardner, MA 01440
(978) 632-5480
www.roadsideamerica.com/tip/2439

Gardner, Mass. is the hub for furniture manufacturing and sales in the area. New England's Biggest Chair, which is 20 feet tall, 10 feet wide, nine feet deep and weighs 3,000 pounds, is found in Gardner. It is a traditional ladder back chair with a reinforced seat that sits in front of an elementary school on the outskirts of Gardner. The Bicentennial Giant Chair is a favorite spot for picture-taking in this town, which is about 60 miles west of Boston.

Related: Boston Area's Best Family-Friendly Bike Trails

Plantation Man-Big White Guy
In front of the Plantation Inn
485 Springfield St.
Agawam, MA 01030
www.roadsideamerica.com/story/11781

The "Plantation Man," as he is known by the Agawam locals, has had several careers, including greeting cars in front of the Plantation Inn in Chicopee as they exit the Massachusetts Turnpike, playing Uncle Sam in front of  Mutual Ford in Springfield, and a pizza chef in Springfield. He is also known as "Southern Man" with his white suit and big white top hat, which has served as an unofficial marker for the C-5As flying into the Westover Air Reserve Base. This "Big White Guy" has moved around a lot and landed in his present location in October 2015.

Big Teddy Bear Statue
In front of Floating Hospital For Children
Tufts Medial Center
750 Washington St.
Boston, MA 02111
(617) 636-5000

Schwartz bear sits in front of the Floating Hospital for Children at Tufts Medical Center in Boston, bringing smiles to all of the children who pass through the doors. The three-ton, button-eyed bronze statue sat at the front door of FAO Schwartz in Boston until it was moved to the present Washington Street location in 2004, when the store closed its doors. The friendly bear is sitting and waving with one paw and holds a stack of three alphabet blocks, F, A and O. It is at the edge of the Washington Street sidewalk, easily visible for those walking or driving by.

Related: Boston's Best Street Art