See two of Brookline's most delightful neighborhoods. Longwood and Cottage Farm provide a quiet, bucolic setting apart from its urban borders. This walking tour showcases a remarkable collection of romantic English country style cottages and picturesque churches.

Brookline was once known as the “Muddy River,” much of it owned by Judge Samuel Sewall (Salem Witch Trials). Starting in 1818, David Sears II purchased 500 acres of Brookline following the construction of the Mill Dam that provided direct access to Boston.

Sears, an admirer of Napolean Bonaparte, planned the neighborhood of Longwood drawing inspiration from the English countryside and planted some 14,000 trees protecting these seasonal cottages “from unsightly and inconvenient neighbors.”

David Sears sold 200 acres of his land to cotton-tycoon Amos Lawrence. The Lawrences developed the land into a residential suburb in which they wanted to live and named it Cottage Farm.

Today, the Longwood and Cottage Farm historic districts span some 119 acres and are comprised of sophisticated suburban homes and cottages designed in the Gothic Revival, Mansard, Queen Anne, and Georgian Revival architectural styles.

Featured on this walking tour are the architectural works of Peabody & Stearns, George Tilden, George Dexter, Samuel Glaser, and the churches of Arthur Gilman and Alexander Estey.

Boston By Foot Brochure listing Boston tours in 2009 season Boston By Foot Guided Walking Tours For Boston By Foot Docents. Explore Boston on a Boston By Foot walking tour. The Dark Side of Boston. Exploring the Charles River Basin.