Where to Propose in Boston

The combination of culture, history, and scenery means that Boston is a fabulous city for a weekend away and is packed with ideal proposal locations. Whether you choose the romantic atmosphere of Beacon Hill with its gas lamps and cobbled streets, the Italian vibe of North End, or the trendy setting of Newbury Street, Boston is a superb place to wander about hand in hand and discover your own perfect place to propose.

Iconic Proposal Locations in Boston

When we imagine Boston the image that most often springs to mind is Acorn Street in Beacon Hill. A cobbled street with brick built row houses which some people suggest is the most photographed street in the U.S. It is certainly a pretty spot for a romantic walk and could be a great place for an evening proposal. If you’re planning a winter proposal, check out the Commonwealth Avenue Mall, a strip of park that runs down the center of Commonwealth Avenue, as the trees there form a beautiful pathway when they are lit up with Christmas lights.

Another iconic location in Boston is the Hatch Shell, or Edward A. Hatch Memorial Shell, an outdoor concert venue located at the Charles River esplanade. There are often free concerts at the Hatch Shell during the summer months and the grass pavilion in front of the stage is a great place to chill out with your girlfriend. For the ultimate in Boston icons, consider proposing at the legendary Fenway Park but only if your girlfriend is a big Red Sox fan and you think she’d be happy with a public proposal. Think about proposing during a ballpark tour and the Winter Lights Show if you’re not sure about proposing during a game.

Boston Common, the oldest park in the U.S and the starting point of the Freedom Trail, along with it’s more picturesque neighbor Boston Public Garden, would both be ideal places for an iconic Boston proposal. Take a swanboat ride at the lagoon in the Public Garden or go ice skating on the Frog Pond on the Common. For an unusual outdoor proposal location why not visit the Arnold Arboretum of Harvard University in the Jamaica Plain area of Boston? There are innumerable beautiful locations within its boundaries for a unique proposal.

Proposing on the Water in Boston

Boston Harbor has a charm all of its own and there are plenty of ways to propose on and around this historic location. You could make a day of it and take a cruise out around the Boston Harbor Islands, or check out some of Boston’s historic sites including the lighthouse and Old North Church where two lanterns were famously hung to show that the British were invading by sea. A sunset cruise is also a great option and the patriotic among you will enjoy the USS Constitution’s sunset cannon fire.

If you’d rather stay off the water there are plenty of locations along its edge that would make great proposal spots such as Carson Beach in South Boston, a sandy beach with a pier and lovely views of Boston Harbor. The Charles River is also a picturesque spot for a proposal, whether you have a picnic on the esplanade, cross over the footbridge to Cambridge, or simply take an evening stroll along its banks.

Proposing with a view of Boston

For a spectacular view over Boston and, on a clear day, the surrounding 100 miles, the Skywalk Observatory at the Prudential Center offers a breathtaking 360-degree panorama. In the summer it is open until 21:30 but do check in advance as it sometimes closes for private functions. Follow a romantic Skywalk proposal with dinner at Top of The Hub.

If you’d like to get out of town but still propose with a view of Boston, there are a couple of places you could go. Just 15 miles from Boston, the World’s End Reservation features rolling hills and rocky shorelines which offer sweeping views of the Boston skyline. Whether you take a summer walk, or go cross country skiing in winter, this area of natural beauty is extremely romantic. You could also consider Robbins Farm Park in Arlington Heights, which is an ideal picnic spot overlooking the landmarks of Boston.

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