Whittemore House

Discover cities like never before.

Enjoy over self-guided city exploration with our app ‘Explory’. Learn all about the history and discover hidden more than 500.000 hidden gems, that only locals know about. Build custom tours, find nearby places, and start exploring instantly.

Once upon a time, this land now occupied by Whittemore House witnessed scenes of colonial life. The Whittemore House, a historic colonial house, stands at 54 Massachusetts Avenue in Arlington.

With its oldest section dating to around 1695, the Whittemore House is one of the town’s oldest houses. It may even be the very oldest. The house was listed on the National Register of Historic Places in 1978. The Whittemore House sits on the south side of Massachusetts Avenue in East Arlington. It is nestled between Fairmont and Lafayette Streets. Notice how it’s set back from the street. The flanking multifamily buildings surround it. It sits slightly askew from the current road.

Let’s take a closer look at the Whittemore House. It is a two-story wood-frame structure. It features a hip roof and a clapboarded front. You can see the brick sidewalls. Interior chimneys pierce the roof. The main facade is symmetrical with five bays. The centered entrance is sheltered by a gabled porch. Fluted columns support this porch.

Jonathan Butterfield, a field driver in Menotomy, built the earliest part of the Whittemore House around 1695. Menotomy was what Arlington was called back then. In 1749, Samuel Whittemore III bought the house. He was the son of a local American Revolutionary War hero of the same name. The famous Whittemore was long thought to own this house. But he actually lived across Massachusetts Avenue.

Around 1845, Greek Revival modifications were made to the Whittemore House. A new porch was added around 1920. Restorations began in 2006 and have since been completed. The house’s position relative to Massachusetts Avenue is unique. It reflects the road’s early 18th-century alignment.

There is also another Whittemore House. The Jacob Whittemore House is located in Minute Man National Historical Park. It is one of eleven witness houses to the battles of April 19, 1775. Those battles kicked off the Revolutionary War. Jacob and Elizabeth Whittemore lived here with their daughter Sarah. Moses Reed, Sarah’s husband, and their three small children also lived there. Jacob and Moses trained with the Lexington Minute Men. But neither fought in the battles that day. Instead, they carried Sarah to a nearby wooded area. She was still dangerously ill 18 days after childbirth. The rest of the family also laid low there until the battle had passed their home.

To the west of the Jacob Whittemore House, Captain John Parker led the Lexington militia. They engaged the British Regulars. The family survived the day. Sarah recovered. Moses went on to serve in the Continental Army. The family lived in the house from about 1716-1718. Jacob’s father, Nathaniel, built it. They lived there until 1780. Then, the family sold it.

The Whittemore Robbins House, another historic site, is a beautifully restored 1800s Colonial mansion. It’s perfect for special occasions. These include weddings, anniversaries, and christenings. It is also great for bar/bat mitzvahs and graduations. It features a spacious side yard. An adjacent Olmstead-designed garden has a capacity of up to 250 people.

So, as we stand here before the Whittemore House, remember its long history. It has witnessed centuries of change. From colonial beginnings to revolutionary times and beyond, the Whittemore House stands as a testament to the enduring spirit of Arlington.

The story of Whittemore House in Boston is just one of many fascinating insights you can discover with Explory. To experience the city beyond its surface, you need more than just a map – you need a smart guide that reveals the background, the culture, and the character of each place. With Explory’s city guide, you can dive deeper into Boston and transform your visit into a unique city tour filled with stories that bring history and everyday life to light. Explory connects you with Boston in a new way. Our guide doesn’t just show you where to go – it enriches your journey with context and atmosphere. Through carefully designed routes and storytelling, you’ll uncover hidden gems and unexpected highlights that even locals might miss. The audio guide makes the city come alive, allowing you to listen while you walk and explore at your own pace. Our city guide is ideal for travelers who want more than sightseeing. Whether your interest is culture, architecture, or local traditions, Explory enables authentic exploration. Each city tour is flexible and intuitive, helping you experience Boston with freedom while still being guided by expert knowledge. By combining narrative, navigation, and discovery, Explory ensures your trip becomes an adventure filled with hidden gems and lasting impressions. Take the next step and download the Explory App today. Inside, you’ll find over 300 cities and more than 500,000 POIs and stories to explore. Whether you’re searching for a reliable guide, want to try an immersive audio guide, or plan a memorable city tour, Explory is your all-in-one companion. Begin your journey now and uncover the true essence of Boston – only with Explory.

More Places in Boston

Middle Brewster Island

Imagine red-roofed houses lining this island. That’s Middle Brewster Island in the 1840s. It was a vibrant fishing community then.

Explore

Chisholm’s Motor Inn

“Seven miles from Boston’s vibrant heart,” I begin, gesturing towards Chisholm’s Motor Inn, “lies a haven for travelers.” Chisholm’s Motor

Explore

Turtle Mural

Behold Myrtle the Turtle a magnificent bronze sculpture. She rests in Beacon Hill’s Myrtle Street Playground. This isn’t just any

Explore

Fairbanks House

Step into the past. Gaze upon the Fairbanks House. This isn’t just any house. It’s the oldest surviving timber-frame house

Explore

Riverside Cemetery

Beneath the gaze of countless granite sentinels, Riverside Cemetery in Saugus, Massachusetts whispers tales of lives lived and legacies left

Explore

Knowles Center

“Law school or architectural marvel?” I wonder what you will say after this tour of the Knowles Center. It is

Explore