Winchester, Virginia, United States of America: What to pack, what to wear, and when to go [2022]
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Traveling to Winchester, Virginia, United States of America? If you're planning to go to Winchester, below is some important information about when to go, what to wear, and what to pack.
Contents
- When to go to Winchester
- Important essentials for Winchester
- Activities for Winchester
- Winchester in January: weather and what to pack
- Winchester in February: weather and what to pack
- Winchester in March: weather and what to pack
- Winchester in April: weather and what to pack
- Winchester in May: weather and what to pack
- Winchester in June: weather and what to pack
- Winchester in July: weather and what to pack
- Winchester in August: weather and what to pack
- Winchester in September: weather and what to pack
- Winchester in October: weather and what to pack
- Winchester in November: weather and what to pack
- Winchester in December: weather and what to pack

About your travel guide
Hi! I'm Dev. I've traveled all over the world and in my travels, I have made many packing lists. In this series, my team and I have compiled the most useful information, as well as things we couldn't live without, to help you plan your trip.
When to go to Winchester, Virginia, United States of America
Based on the climate and weather in Winchester, the best time to go is September. See below for details.
Important essentials for Winchester, Virginia, United States of America
Here are some general tips on what to wear in Winchester, as well as several items to remember to pack when traveling there.
COVID-19 ESSENTIALS FOR 2022
Travel insurance
If you or a companion get COVID-19, your amazing trip can be ruined. Good travel insurance can help. See plans
-
A vaccine card protector
Vaccine cards can wear away. An unreadable vaccine card can have severe consequences. This vaccine card protector helps avoid that.
-
Kids' KN95 masks
N95 masks aren't sold for kids. These are a good alternative (and can also be used by adults if N95 masks are not available).
-
Hand sanitizer
This hand sanitizer is a good TSA-friendly option.
-
Travel disinfecting wipes
Use these to sanitize plane and hotel surfaces.
-
N95 masks to use in crowded airports
These N95 masks provide the best level of protection possible.
General health necessities
Don't forget these
-
Power bank for devices
A portable power bank, like this one
-
For families with young children
-
Money/passport pouch
A money pouch is vital for protecting your passport and credit cards.
-
Plug adapter
A plug adapter that supports outlet types A and B. This one should work in most locations, but you may want to check with your hotel.
-
Airplane or car necessities
-
Voice and data SIM card
A SIM card that works in Winchester. A good global SIM card works in most countries, but check the country list before buying.
What to wear/what to pack for Winchester, Virginia, United States of America by month
Already know when you're traveling?
January
January in Winchester can be very chilly. The rain/snow can amount to several inches/centimeters. During this time, temperatures average in the low 40s F (single digits C), although night temperatures can dip into the low 20s F (single digits below 0 C).
What to wear/what to pack:
-
Lip balm
Our pick is: here
-
Heavy jacket
-
Sweaters
-
Insulated water bottle
Our best choice:
-
Warm pants or jeans
-
Heavy socks
Such as:
-
Gloves
-
Cold weather footwear
-
Waterproof snow boots
In addition to standard shoes, you should bring snow boots. For traveling to Winchester (Virginia), we suggest these boots:
-
Waterproof jacket that can be used in snow
-
A windproof umbrella
This is worth investing in for this weather. This one is a great option.
If you see the Shenandoah Discovery Museum, wear museum-appropriate clothing and take:
-
Comfy walking shoes
-
Ultralight day pack
Like this, so you don't have to lug around a heavy suitcase.
-
Small portable cooler
Save money on drinks with this portable cooler.
February
February in Winchester can be very chilly. The rain/snow can amount to several inches/centimeters. During this time, temperatures average in the 30s F (single digits C) to 40s F (single digits C), although night temperatures can dip into the low 20s F (single digits below 0 C).
What to wear/what to pack:
-
Insulated water bottle
Our first choice:
-
Gloves
-
Heavy jacket
-
Warm pants or jeans
-
Sweaters
-
Lip balm
Our favorite option: here
-
Heavy socks
Such as:
-
Cold weather footwear
-
Waterproof snow boots
In addition to day-to-day shoes, it's important to bring snow boots. For travel to Winchester (Virginia), a great option is these boots:
-
Waterproof jacket that can be used in snow
-
A wind resistant umbrella
This is something you need here. This one is a great option.
If you see the Shenandoah Discovery Museum, wear museum-appropriate clothing and take:
-
Comfy walking shoes
-
Ultralight day pack
Like this, so you don't have to lug around a heavy suitcase.
-
Small portable cooler
Save money on drinks with this portable cooler.
March
March in this region can be brisk. Temperatures average in the low 50s F (low 10s C) during the day.
What to wear/what to pack:
-
Warm pants or jeans
-
Light gloves or mittens
-
Lip balm
In our opinion, the best choice: this one
-
Extra socks
-
Fleece
-
Jacket or coat
-
Standard footwear
-
Waterproof snow boots
In addition to regular footwear, it's important to bring snow boots. For travel to Winchester (Virginia), we suggest these boots:
-
Waterproof jacket that can be used in snow
-
A windproof umbrella
This is essential in this type of weather. This one is a great choice.
If you see the Shenandoah Discovery Museum, wear museum-appropriate clothing and take:
-
Comfy walking shoes
-
Ultralight day pack
Like this, so you don't have to lug around a heavy suitcase.
-
Small portable cooler
Save money on drinks with this portable cooler.
April
If you go to Winchester in April, you will notice that it is chilly. Daytime temperatures are in the 60s F (high 10s C).
What to wear/what to pack:
-
Pants or jeans
-
Extra socks
-
Standard footwear
-
Light and heavy skirts
-
Long sleeve shirts or blouses
-
Light jacket or fleece
-
Dresses
-
A rain coat to layer with another jacket
-
100% waterproof footwear
We suggest these rain boots:
-
Rain pants
These will be essential in heavy rain.
-
Waterproof phone bag
-
Wind resistant umbrella
This one is a perfect one to buy.
-
Waterproof bag/luggage cover
So your belongings remain dry. We recommend:
If you see the Shenandoah Discovery Museum, wear museum-appropriate clothing and take:
-
Comfy walking shoes
-
Ultralight day pack
Like this, so you don't have to lug around a heavy suitcase.
-
Small portable cooler
Save money on drinks with this portable cooler.
May
If you vacation in Winchester during May, you are likely to notice that it is mild. Temperatures tend to hover around the low 70s F (low 20s C) during the day, while at night they can dip into the low 50s F (low 10s C).
What to wear/what to pack:
-
Light skirts
-
Sandals
-
Sunscreen lotion
-
Short pants or heavy shorts
-
Light dresses
You can find some great options here
-
Long and short sleeve shirts
-
Bug repellent
-
Extra socks
-
Breathable footwear or sandals
-
A rain poncho to layer with a coat
-
100% waterproof footwear
We like these rain boots:
-
Rain pants
These pants can be vital in heavy rain.
-
Waterproof phone bag
-
Umbrella
This one is a great choice.
-
Waterproof bag/luggage cover
So your things stay dry. We suggest:
If you see the Shenandoah Discovery Museum, wear museum-appropriate clothing and take:
-
Comfy walking shoes
-
Ultralight day pack
Like this, so you don't have to lug around a heavy suitcase.
-
Small portable cooler
Save money on drinks with this portable cooler.
June
In June, Winchester is extremely warm. Temperatures routinely are in the low 80s F (high 20s C) and once in a while jump into the low 90s F (low 30s C) range. At night, lows are in the low 60s F (mid 10s C). This is also a rainy time for Winchester, with several of the days of the month having rain.
What to wear/what to pack:
-
Short pants or heavy shorts
-
Sandals
-
Bug repellent
-
Breathable footwear or sandals
-
Light dresses
You can find some great options here
-
Sunscreen lotion
-
Light skirts
-
Long and short sleeve shirts
-
Extra socks
-
A rain coat to layer with another jacket
-
100% waterproof footwear
We use these rain boots:
-
Rain pants
Rain pants can be vital in heavy rain.
-
Waterproof phone bag
-
Windproof umbrella
This one is a perfect one to buy.
-
Waterproof bag/luggage cover
So your things remain dry. We suggest:
If you see the Shenandoah Discovery Museum, wear museum-appropriate clothing and take:
-
Comfy walking shoes
-
Ultralight day pack
Like this, so you don't have to lug around a heavy suitcase.
-
Small portable cooler
Save money on drinks with this portable cooler.
July
In July, Winchester is constantly hot. Temperatures routinely are in the 80s F (low 20s C) and a bit less than half of the time jump into the low 90s F (low 30s C) range. At night, lows are in the 60s F (high 10s C). This is also a rainy time for Winchester, with several of the days of the month having rain.
What to wear/what to pack:
-
Sunscreen lotion, moderate SPF
-
Insulated water bottle
Our favorite also removes contaminants:
-
Waterproof sandals
-
Breatheable shirts
A breathing shirt can cool you down quickly and protect you from UV rays:
-
Bug repellent
-
Cool and dry dresses
These dresses to provide UV protection and keep you cool.
-
Sunglasses
-
Skirts
-
Loose-fit shorts
-
A rain jacket to layer with another jacket
-
100% waterproof footwear
We suggest these rain boots:
-
Rain pants
Rain pants are essential in a rainstorm.
-
Waterproof phone bag
-
Wind resistant umbrella
This one is a great choice.
-
Waterproof bag/luggage cover
So your bags remain dry. We suggest:
If you see the Shenandoah Discovery Museum, wear museum-appropriate clothing and take:
-
Comfy walking shoes
-
Ultralight day pack
Like this, so you don't have to lug around a heavy suitcase.
-
Small portable cooler
Save money on drinks with this portable cooler.
August
August in Winchester is extremely warm. The rain can amount to several inches/centimeters. During this time, temperatures average in the 80s F (high 20s C), although night temperatures can dip into the low 60s F (mid 10s C).
What to wear/what to pack:
-
Breatheable shirts
A cooling shirt can keep you comfortable and protect you from the sun:
-
Loose-fit shorts
-
Sunglasses
-
Sunscreen lotion, moderate SPF
-
Waterproof sandals
-
Insulated water bottle
Our choice also cleans contaminants:
-
Skirts
-
Cool and dry dresses
These dresses include UV protection and help you stay cool.
-
Bug repellent
-
A rain jacket to layer with a coat
-
100% waterproof footwear
We recommend rain boots:
-
Rain pants
These pants are essential in a storm.
-
Waterproof phone bag
-
Umbrella
This one is a great choice.
-
Waterproof bag/luggage cover
So your things don't get wet. We suggest:
If you see the Shenandoah Discovery Museum, wear museum-appropriate clothing and take:
-
Comfy walking shoes
-
Ultralight day pack
Like this, so you don't have to lug around a heavy suitcase.
-
Small portable cooler
Save money on drinks with this portable cooler.
September
If you are traveling to Winchester in September, you will notice that it is warm. Daytime temperatures are in the high 70s F (mid 20s C).
What to wear/what to pack:
-
Breathable footwear or sandals
-
Light dresses
You can find some great options here
-
Sandals
-
Sunscreen lotion
-
Light skirts
-
Short pants or heavy shorts
-
Extra socks
-
Bug repellent
-
Long and short sleeve shirts
-
A rain poncho to layer with a jacket
-
100% waterproof footwear
We like these rain boots:
-
Rain pants
These pants can be vital in a storm.
-
Waterproof phone bag
-
Umbrella
This one is a perfect choice.
-
Waterproof bag/luggage cover
So your bags stay dry. We like:
If you see the Shenandoah Discovery Museum, wear museum-appropriate clothing and take:
-
Comfy walking shoes
-
Ultralight day pack
Like this, so you don't have to lug around a heavy suitcase.
-
Small portable cooler
Save money on drinks with this portable cooler.
October
October in Winchester is mild. The average overnight temperatures in the area are in the 40s F (single digits C), with a few days below 32 F (single digits C).
What to wear/what to pack:
-
Long sleeve shirts or blouses
-
Light jacket or fleece
-
Pants or jeans
-
Extra socks
-
Light and heavy skirts
-
Standard footwear
-
Dresses
-
A rain jacket to layer with another jacket
-
100% waterproof footwear
We like these rain boots:
-
Rain pants
These pants can be essential in a rainstorm.
-
Waterproof phone bag
-
Umbrella
This one is an excellent choice.
-
Waterproof bag/luggage cover
So your bags remain dry. We recommend:
If you see the Shenandoah Discovery Museum, wear museum-appropriate clothing and take:
-
Comfy walking shoes
-
Ultralight day pack
Like this, so you don't have to lug around a heavy suitcase.
-
Small portable cooler
Save money on drinks with this portable cooler.
November
November for Winchester is cool. Temperatures average in the 50s F (low 10s C) during the day.
What to wear/what to pack:
-
Extra socks
-
Warm pants or jeans
-
Jacket or coat
-
Lip balm
In our opinion, the best choice: here
-
Fleece
-
Light gloves or mittens
-
Standard footwear
-
A rain coat to layer with another jacket
-
100% waterproof footwear
We recommend these rain boots:
-
Rain pants
These are a lifesaver in a storm.
-
Waterproof phone bag
-
Wind resistant umbrella
This one is a perfect option.
-
Waterproof bag/luggage cover
So your suitcases remain dry. We suggest:
If you see the Shenandoah Discovery Museum, wear museum-appropriate clothing and take:
-
Comfy walking shoes
-
Ultralight day pack
Like this, so you don't have to lug around a heavy suitcase.
-
Small portable cooler
Save money on drinks with this portable cooler.
December
December for Winchester can be very chilly. Temperatures average in the 40s F (single digits C) during the day.
What to wear/what to pack:
-
Warm pants or jeans
-
Heavy jacket
-
Gloves
-
Lip balm
Our pick: this
-
Sweaters
-
Heavy socks
Such as:
-
Insulated water bottle
Our best choice:
-
Cold weather footwear
-
Waterproof snow boots
In addition to day-to-day footwear, it's important to bring snow boots. For travel to Winchester (Virginia), we suggest these boots:
-
Waterproof jacket that can be used in snow
-
A windproof umbrella
This is worth investing in for this weather. This one is a perfect option.
If you see the Shenandoah Discovery Museum, wear museum-appropriate clothing and take:
-
Comfy walking shoes
-
Ultralight day pack
Like this, so you don't have to lug around a heavy suitcase.
-
Small portable cooler
Save money on drinks with this portable cooler.
Activities for Winchester, Virginia, United States of America
Here are some activity recommendations and activity-specific packing tips for Winchester.
Check out our guides for these other locations: South Sound, Washington, United States of America, Schweinfurt, Germany, Detroit Lake State Recreation Area, Oregon, United States of America, Sagard, Germany, Khorasan, Iran, Vereya, Russia, El Dorado Hills, California, United States of America, Latgale, Latvia, Valdes Peninsula, Argentina, Floyd, Virginia, United States of America, and Nanao, Japan.