Downtown Winthrop, Massachusetts









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Shop Downtown Discount Card

Discounts For Customers - Support Local Businesses - Fight Cancer

When you purchase a Shop Downtown Discount Card for $10, you help support your neighbors, local economy and the American Cancer Society's mission to save lives, celebrate lives and lead the fight for a world without cancer. You also ensure great savings on a variety of products and services every time you patronize a participating member. It's a win/win situation.

Shop Downtown will contribute 100% of the sale price of each discount card sold through December 31, 2021, to American Cancer Society Relay For Life. The American Cancer Society does not endorse any product or service.









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Things to do in Winthrop, Massachusetts

Main Street of old Downtown Winthrop speaks to once what was and what could be once again. As Winthrop the community gathers, it leaves a pocket of opportunity for small business owners to come in and set up shop.Take a few minutes to explore what each downtown has to offer by viewing our directory below.

Downtown Winthrop brings musicians together and finding your local musical instrument shop can be a great way to get to try new and used guitars. Be sure to start your search downtown if you are looking to upgrade, trade-in or add to your collection.

Downtown Winthrop makes shopping for wine and other spirits easy by bringing an incredible collection sourced from local, regional well-known producers from around the World. Hit the wine tasting events and stock up on your favorite choice to be shipped home for your convenience.

Downtown Winthrop has that special dining venue and you are sure to find something to please with numerous meals served to satisfy each palette. A wide variety of restaurants and delis are available to choose from with a nice selection of entrees and especially desserts.

Downtown Winthrop offers on-the-go dining when you visit your favorite food truck. Pick up some corn tortilla tacos with freshly made pico with a fresh squeeze of lemon to give your day a boost. Food trucks can offer a wide variety of niche ethnic blends.

Why do you love downtown?

Daniel E Swanson
The Downtown area stores are friendlier and have comparable pricing as the bigger stores. The only problem is parking and the distance you may have to walk to do your shopping.

Kathleen Townsend
It's so quaint and cute!

Alison Barlow
Charming, lovely downtown. Love the antique shops!

Diane morgon
We are coming to visit and looks very interesting.

Kara Braud
Beautiful place!

Restaurants in Winthrop, Massachusetts


Alia Ristorante

495 Shirley St
Downtown Winthrop



Amanda Oakleaf Cakes

1 Pauline St
Downtown Winthrop



Bamboo

4 Somerset Avenue
Downtown Winthrop



Anacone Restaurant Co

308 Shirley St
Downtown Winthrop




Downtown Winthrop Hotels

Finding the best hotel in Downtown Winthrop can make or break the experience of your entire trip. Take a few minutes to explore what each hotel has to offer by viewing our directory below. Here are some tips to consider:

Always announce during booking if the trip is for a special event, anniversary or reunion. Group rates can be pre-negotiated and you may qualify for a lower cost and better upgrades for your stay. If you are the one setting up the event, always work directly with the front desk manager to make sure the best service is offered to your party.

Policies vary on the availability of pet friendly rooms to it is wise to be open, honest and upfront during the booking process. You may find yourself kicked out or even paying a large deposit if you are not in a pet-friendly hotel and bring one anyway. New ADA laws are fuzzy though as service animals are not required to be documented and proprietors are legally not allowed to ask if the animal is a pet vs. a service animal.

Ask to be shown a room before you check-in which signals the front desk agent to show the best room available to sell it right away. This can put you in the best room available at that time and gives you the ability to check for cleanliness, smells and sounds before transacting with the hotel.