All About Living in Middlesex County, Massachusetts

Middlesex South Registry of Deeds, East Cambridge Massachusetts Source: Wikimedia Commons

Named for the historic county in the southeast of England, Middlesex County, Massachusetts was created as a county in 1643, predating both the Revolutionary War and the signing of the Declaration of Independence. It is the second-oldest county in the United States of America, beat only by St. Mary’s County in Maryland, established 6 years prior. Not only that, but in 1775, the first armed conflict of the American Revolutionary War occurred in Middlesex County.

Not only is history prevalent here, but Middlesex County also has some of the best schools in the country, impeccable restaurants, fun seasonal activities for the whole family, great entertainment and museums, and accessibility to nearby cities, making this one of the best places to live in all New England.


Children walking toward school bus

Middlesex County is the second-best public school district in the Commonwealth of Massachusetts, with incredible K-12 schools like Field Elementary School, Weston Middle School, Frederick J. Dutile School, Marshall Middle School, Billerica Memorial High School, Lexington High School, and more. The schools near Aspen Regency will fall under the Billerica Public School District, with phenomenal schools and student-teacher ratios. There are fantastic private schools available as well!

Harvard University graphic

With the past influencing the present and future all around New England, Middlesex County has some of the best and oldest colleges and universities in the country. Home to Harvard University (the oldest higher learning institution in the United States), Tufts, Brandeis, and Massachusetts Institute of Technology, there’s no shortage of top-tier higher educational opportunities.


Massachusetts has incredible hiking and walking trails. For an easy afternoon walk, visit the Oak Hill Conservation Site in Littleton. You’ll be able to view the natural flora and fauna from several marked trails. With more than 100 miles of mixed-use trails, you can tour Middlesex Fells Reservation for biking, hiking, canoeing, kayaking, cross-country skiing, horseback riding, sailing, and more. There’s even an off-leash dog park for your furry friends to run around. If you’re looking for even more walking and hiking trails, take a trip to Lowell-Dracut-Tyngsboro State Forest. This forest is spread across 3 towns, spanning more than 1,000 acres with over 6 miles of trails for you to explore. Go fishing or boating in the ponds, swamps, and wetlands.

Seasonal Information

Country Road

Massachusetts is known for stunning foliage-filled falls, gorgeous snowy winters, mild sunny springs, and positively beautiful summers. If you’re looking for things to do in any season, we’ve got you covered.

Colder Months

In the fall, we’re often looking for the best spooky spots to test our mettle, or for places to see the fall foliage in all its glory in the Minuteman National Historic Park. But what if we want to partake in some winter activities as well? Visiting the Nashoba Valley Ski Area will surely give you the rush you’re seeking, whether in a snow tube, on skis, or snowboard. For more holiday-centric fun, you can check out the Zoo Lights at Stone Zoo in Stoneham to see stunning holiday lights and decorations, or go to the City of Lights Parade and Holiday Celebration in Lowell.

Warmer Months

Louisa May Alcott Orchard House Source: Yelp

Surround yourself with history in Concord, MA in the warmer months. You can visit Orchard House, where Louisa May Alcott wrote Little Women. Stroll around Walden Pond and learn about Thoreau, or even jump in for a swim. Learn about the African American history of Concord at The Robbins House. For those who are looking to float around, take your kayaks out to Long Sought-for Pond in Westford for a paddle, a swim, or some fishing.


Merrimack Rerpetory Theater Source: Yelp

If you want to watch Ivy League football, visit Harvard Stadium in Cambridge to watch the Harvard Crimson compete against other NCAA teams, notably their rival, the Yale Bulldogs. For theater buffs, a night spent at the Merrimack Repertory Theater in Lowell is sure to satisfy all cathartic art needs. You’ll find something for everyone here: kids’ shows, musicals, plays, and more.


Buckman Tavern in Lexington Source: Wikimedia Commons

For the history buff, Massachusetts is a dream. As the birthplace of the American Revolutionary War, there’s no shortage of historical museums and structures in Middlesex County. Buckman Tavern in Lexington is where Captain Parker and his militia waited in the wee morning hours of April 19, 1775 to anticipate the British Redcoats. The tavern itself dates back to 1709.

Discovery Museum in Acton, MA, is an interactive children’s museum. With both indoor and outdoor museum spaces, kids can learn about history, science, art, music, and more, all while being encouraged to interact with the exhibits and experiences. There are also specialty hours with free admission for families with disabilities, ensuring that everyone is able to enjoy the museum in whichever way works best for them.


80 Thoreau dining area Source: Yelp

While we’re sure you’ve learned all about the great eats in Billerica, MA, there are other restaurants throughout Middlesex County that we feel you should know. 80 Thoreau in Concord offers an impeccable dinner menu from Tuesdays through Saturdays. You will have a one-of-a-kind culinary experience in this rustic, chic space offering creative “farm-to-fork” American cuisine. With a small, seasonally-curated menu, you can rest assured that every meal is purposefully created with the perfect bite in mind.

The Farmer’s Daughter in Sudbury offers more farm-to-table delicacies ready to satisfy and stimulate your taste buds. They are open for brunch and lunch Wednesdays through Mondays, ensuring your weekend brunch plans are confirmed. You’ll see on their walls a board with information about the farms where they procure their meat, produce, dairy, bread, coffee, and more. They’re committed to keeping it local.

Public Transportation

Much of Middlesex County is close to metropolitan Boston, allowing for access to the city via public transportation. Commuters have an easy time traveling from their homes to offices or meetings in Boston using the Massachusetts Bay Transportation Authority (MBTA) Commuter Lines. Getting to and from both North and South Stations for work, entertainment, dining, and more is a breeze. Further north into the county, you have access to the Lowell Regional Transit Authority (LRTA), offering routes in and out of Lowell.