Downtown Wolfeboro

HISTORICAL VIEWS LOOKING SOUTH ON MAIN STREET

The third gallery photo shows a sign for Tobey’s Pharmacy, which survived from the early 1900’s into the 1960’s. At the time of the earlier, 1950’s, fourth gallery photo below, the store was temporarily part of the Rexall chain of drug stores. After peaking in 1958 with 11,158 stores, the Rexall franchise gradually faded away over the ensuing decades.

Black and white version of previous photo

The same view is labeled differently, either looking south, previous, or looking east. The view is to the southeast.

Brewster Memorial Hall

Built in 1890, Brewster Memorial Hall, also known as the Wolfeboro Town Hall, is seen at the top of many of the above views looking South. The building is still the home of Wolfeboro’s municipal offices. The clock tower still functions and features a bell made by Paul Revere which rings out every hour.

Wolfeboro’s nearest neighbor, Alton, has a nearly identical clock tower. Like the tower in Wolfeboro, the building, built in 1894, serves as the town hall, and as in Wolfeboro, the clock continues to function.

The Alton Town Hall on the evening of April 21, 2026.

HISTORICAL VIEWS LOOKING NORTH ON MAIN STREET

Post Office Square

Postcards of Wolfeboro’s Post Office Square, circa 1905 to circa 1925. The large, 3-story building at the center was known as the “Peavey Block”. The prominent, still-standing building looms over Wolfeboro’s waterfront. The building housed the Wolfeboro P.O. from 1894-1936. The exact age of the building is unknown, but it was built prior to 1889, when it appeared on the map shown below.

National Bank Building

The Lake National Bank. One of the oldest buildings in Wolfeboro, it was buiilt in 1855 and still stands today, but is no longer a bank. The building has been the home of a multitude of businesses over the years.

AI colorized and enhanced photo of the bank building, which fronts on South Main Street, circa 1873. Railroad Ave is to the left of the building, and Central Ave is to the right. The Wolfeboro train station is seen on the left edge of the photo, and a bit of the Elmwood Hotel is seen on the right.

The Goodwin Block was located on Central Ave. The Elmwood Hotel is just off-photo to the left.

By the time of these colorized postcards, the bank had replaced the four, single-window dormers on the rooftop with two triple-window ones.

Black’s Gift Shop

The second photo is of the antique auto seen in the photo of Black’s on the upper right of the photo collage. The view is looking South on Main Street.

The Wolfeboro Post Office

Built in 1936, the current Wolfeboro Post Office on South Main Street was the fifth location for the P.O. since postal service started in Wolfeboro in 1820. Previously, the P.O. had been located in the Peavey Block.

Hotel Elmwood

The Hotel Elmwood (1872 – 1933) stood where the Wolfeboro Post Office is today. It had three earlier names. When the hotel was built in 1872, it was known as the Glendon House. It became the Wolfeboro Hotel in 1895; the Hobbs-Is-Inn in 1906; and then the Hotel Elmwood in 1909.

View of Clow’s Mill from the Hotel Elmwood

View of Hotel Elmwood from Town Hall

Wolfeboro Aerial Photos Gallery

These 1960’s close-up aerials of Main Street show the four principal buildings at the center of town, seen throughout the above photos: the Peavey Block, Tobey’s Pharmacy, Black’s Gift Shop, and the Wolfeboro National Bank. Here one can also still see the tracks of the former Wolfeboro Railroad entering town along the east side of Back Bay and ending at Wolfeboro Station. In 1880, the tracks were extended a short distance past the Wolfeboro station, down Railroad Ave and to the wharf, where one could board the old Mount Washington steamer. The track extension passed between Black’s and the National Bank building, crossed South Main Street, then passed between the Peavey Block and Tobey’s before reaching the lake. The track extension was removed in the mid-1940’s.

The first station on the wharf was a large building that served as a freight depot and a waiting room for passengers of both the Lady of the Lake and Mount Washington steamers. The building also featured offices and many retail shops, including a pool hall, a saloon, a laundry, a dance hall, and a roller skating rink. On May 28, 1899, the building burned, in what was one of the most devastating fires in Wolfeboro history. The second station on the wharf, the much smaller Lake Station, was built in 1903, and was mainly just a freight depot. After freight service to the wharf ended in June 1942, the Lake Station was torn down. In 1948, the empty wharf was filled with a new building, the seasonal Dockside Restaurant.

The Boston & Maine Railroad wharf building. Burned down in 1899.

The Lake Station on the Wolfeboro wharf. Razed in 1942.

The Dockside Restaurant building was built in 1948. Still standing and serving hungry customers in the summertime.

The Wolfeboro Railroad began operations on August 19, 1872. The 12-mile-long line began in Sanbornville, where it branched off from the main B&M railroad line to Conway. Regular passenger service ended on May 16, 1936. Freight operations continued after 1936, but dwindled steadily over the years, until only two small manufacturers of wood products remained as freight customers. In 1972, the line began to once again carry passengers, when a tourist service started up. New owners in 1979 continued the tourist service, which lasted until October, 1985, when all service on the line finally ended. In 1992, local groups began work on converting the abandoned line to a rail trail. Their efforts were successful, resulting in the Cotton Valley Rail Trail, which was completed in 2017.

Click here for a gallery of images and here for a history of the Wolfeboro Railroad.

Aerial photos of downtown Wolfeboro in the late 1930’s. Notice the old Mount Washington steamer docked at the wharf in the first two photos.

A detail from an 1889 map of Wolfeboro resembles an aerial photo. Depicted in the map are two steamships – the Lady of the Lake at the dock, while the Mount Washington approaches from the bay. The Glendon House is numbered 13. Town Hall is numbered 2. The Lake National Bank building is numbered 9. The Peavey Block is numbered 35. The huge factory building on the Back Bay, numbers 24 and 25, housed two different shoe companies. Both companies specialized in ladies and childrens shoes.

The Cropley and Monroe shoe factory was built in 1884. The front section was 200′ wide by 36′ deep, while the ells on either side were 75′ wide by 36′ deep. The building did not last long. On August 9, 1889, the factory burned down, shortly after the above map was published.

Main Street Bridge

The bridge that separates Lake Winnipesaukee from Wolfeboro’s Back Bay, and that also marks the boundary between North Main Street and South Main Street.

The bridge in the 1920s