The small towns of Gloucester and Ipswich are located 20 minutes from one another and are one of our favorite spots to go outside of Boston.
Due to their close proximity you can see both as a day trip from the city, but if you really want to enjoy all they have to offer, spending a night in the area would be your best bet.
Traditional Gloucester and Cape Ann’s Stunning Landscape
Gloucester is located only 45 minutes from Boston and it is well known for its fishing industry. Because of a very large influx of Portuguese and Italian immigrants, the town has many traditional festivals and also various shops where you can buy products directly sourced from these countries.
We frequently drive all the way there to buy their locally made Portuguese sausages and cooking oils called Azeite.
Gloucester is located along a small peninsula called Cape Ann. As you drive along the peninsula, a few minutes from town, you will notice how beautiful and grandiose some of the houses are. A few of these were former private homes that now have become museums which are worth a stop.
I was not originally a fan of touring historic houses, but Massachusetts changed my mind.
While visiting Gloucester, check out Beauport: The Sleeper-McCann House, for one of the most striking interiors you will ever see and then go to Hammond Castle. As you explore its rooms you will understand why it was built by an inventor.
At the edge of the peninsula is Eastern Point Lighthouse. Take a short drive along a “private road” towards a Yacht Club and drive passed it to find the lighthouse. From there, you can walk along its extremely long breakwater; go by the occasional fishermen, until you see sweeping views of the ocean.
Exploring Ipswich and Sampling Traditional Farms
Founded in 1633 and twenty minutes north is the historical town of Ipswich. Its quaint downtown is wonderful for a leisurely stroll and even though small, it has a good number of places to eat and shop.
Try Five Corners Café & Deli, a local sandwich shop selling a variety of hearty subs and Zumi’s Espresso & Ice-cream, a coffee shop specializing in organic coffee sourced from many different countries.
In the heart of downtown, make sure to check out Choate Bridge, one of the oldest surviving stone bridges in the country built in 1764.
Ipswich is also surrounded by a vast rural landscape and gorgeous residential neighborhoods. Many of the houses built in and around the town are historic landmarks. If you interested in experiencing a traditional New England farm, try Russell Orchards.
The family-owned farm is a popular spot for fresh apple doughnuts, hot cider, pies and local vegetables.
One of the oldest and continuing operating farms in the country is Appleton Farms. It has 133 acres of land featuring grazing pastures, historical buildings, trails and a dairy store. Try their Sunset Hill Triple Cream Cheese, made from Jersey Cow’s milk.
It is a brie-like cheese that is very rich and super creamy.
If visiting the estates in Gloucester are not enough for you, consider at stop at Castle Hill, located on the expansive Crane Estate. This remarkable landmark was the summer home of Richard T. Crane and now offers moderate hiking trails that lead to different beaches including Crane Beach.
To visit this 59-room house, you have to take a guided tour, but you can walk as you please throughout its grounds and trails. Castle Hill and its surroundings are so vast that part of you will not believe it was just a summer home!