Downtown Cheshire, Connecticut











Shop Downtown Discount Card

Discounts For Customers - Support Local Businesses - Fight Cancer


Brochure - Research Dollars at Work - Online Patient Programs


When you purchase a Shop Downtown Discount Card, 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 can get great savings on a variety of products and services every time you patronize a participating member. It's a win/win situation.

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

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Things to do in Cheshire, Connecticut

Main Street of old Downtown Cheshire speaks to once what was and what could be once again. As Cheshire 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 Cheshire 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.

Downtown Cheshire shopping is better than online shopping so that you can touch, feel, smell and taste as an experience with an item before deciding to purchase it for yourself or as a gift. Local merchants have hand selected their inventory to provide a unique selection for your downtown.

Downtown Cheshire hosts several events per year for your listening enjoyment but visit your piano shop to learn how to play and possibly purchase your grand, upright or digital piano. Don't forget the specialty work involved such as tuning and moving which are performed by skilled technicians.

Downtown Cheshire can warm you up on a cloudy day or simply offer your daily perk by visiting your local coffee shop. Quality, purity and punch are targeted with coffee beans curated globally and locally roasted while being served fresh as it is made right in front of you. Order up!

Why do you love downtown?

Susan Sunday
Adorable - been 1x and going back tomorrow with my friends

Darle & Tom Warta
Convent, close, & friendly people!

Crystal Wood
Always rich in diversity and intriguing in atmosphere, it's busy, lively and full of color and wonderful aromas! A great experience for the senses.

Jeremy Holmes
Supporting small business downtown is a very real way to support your local community. Downtown businesses are locals, like us.

Sandy saltzer
Great shopping

Restaurants in Cheshire, Connecticut


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1721 Highland Avenue
Downtown Cheshire




Downtown Cheshire Hotels

Finding the best hotel in Downtown Cheshire 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:

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.

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.

Upon check-in, slip the desk agent a tip and ask for the best room they can find at your current booked rate. Often times a quick $10 or $20 bill can go a long way towards the mood of the person who directly decides where you lay your head for the night.