Downtown Winthrop, Massachusetts

Discover shopping, dining, and accommodation in downtown Winthrop.

Plan your trip in Winthrop using Travique: AI Powered Planner



Moving to Winthrop?

Order a Free Relocation Guide




We are seeking partnerships with forward-thinking city officials and business leaders to replicate
our system in their downtowns and launch cities together.

Shop Downtown Discount Card

ShopDowntown.org Discount Card Program

The ShopDowntown.org Discount Card Program encourages local shopping by offering exclusive savings at participating downtown businesses. Shoppers can obtain a discount card by donating $20 or more to the American Cancer Society, unlocking deals of up to 15% off at local stores. The program supports small businesses, funds community health initiatives, and helps strengthen the local economy, making it a win-win for both merchants and consumers.

Shop

0 results

Hotels

Inn at Crystal Cove

600 Shirley Street

Winthrop, Massachusetts

Suburban Extended Stay Logan Airport

312 Shirley St

Winthrop, Massachusetts

Hotel Tips

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.

Bring an actual credit card to avoid deposits and pre-authorizations consuming money in your checking account which will reduce your available balance. Hotels that accept paper cash often ask for a hefty deposit to cover potential damages in your room leaving you scrambling to find an ATM.

Call ahead to make sure your reservation is still active and rebook if there are any price drops or changes in number of people staying with you. Another cost saving tips is to bundle the stay with airport parking and shuttle to avoid hefty fees.

Things To Do

Winthrop brings a custom fit every time a shoe is bought locally. Nothing beats the hands on experience of shoe shopping to add to your collection of Men's, Women's and Children's shoes. Try them on, walk around and make sure you have the best fit as every manufacturer is a bit different on sizing.

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.

Winthrop brings smiles by way of doughnuts and pastries made fresh daily for your enjoyment. Everyone has their favorite of course but having a variety of bakeries is what makes downtown so special. Fritters, scones and pies oh my!

Why Do You Love Downtown?

Jolette Kosier

We are coming to Anoka this weekend we would like to see what this area has to see and enjoy.

Robby

High quality group of restaurants and wonderful shops! Authentic old fashioned down-town atmosphere brings it all together very well.

Angela Corrigan

Convenient, friendly. Stayed at Kermit inn.

Alicia Hansen

I love the unique products and small town vibe.

Carol Rotas

OSF

Join our newsletter

Support Cancer Research

The American Cancer Society does not endorse any product or service.