Winter Getaway to the Berkshires

In a pandemic year when travel has been restricted and our wanderlust has been fierce, we have found that small changes of scenery are good for refreshing everyone’s spirits! That was pretty easy to do over the summer with our annual trip to Narragansett, but now six months later (and still in a pandemic!) we found ourselves in need of another getaway. We haven’t done much winter traveling before, aside from our annual Christmas trips to New York City, and we aren’t a big skiing family. We didn’t want to worry about quarantine and testing requirements across state lines, so we decided on the Berkshires as our destination.

The little kids and I drove out on Friday afternoon, right after they had finished school for the day. Zach and Erin followed later that evening after her dance rehearsal. We did a quick easy on/easy off detour in Chicopee for an early dinner at the Chick-Fil-A drive-thru, which ended up being a highlight of the trip for the kids (clearly we don't do a lot of drive-thru!)  Side note - there is also a drive-thru Friendly’s at the same exit, which was very tempting!

It was a little hairy arriving after dark because we weren’t expecting the road closure detour on Interlaken Road and the whole area is pretty dark in the evenings, but the house was well-lit and welcoming when we pulled up. Traveling for a week, we really settled in and made ourselves at home. I posted separately about my winter adventures packing list (spoiler alert - it's very different than my European capsule packing list!) and how we search for vacation rental houses.


Our Highlights...
We had a long weekend at the start of our trip so we tried to do some of our bigger adventures on Saturday, Sunday, and Monday when we had the entire days free. We tackled smaller hikes and afternoon activities during the week. We headed home the following Sunday morning, so we were there for nine nights total - benefits of remote school/work!

• Saturday: Grocery delivery, No. 6 Depot takeout breakfast, Olivia’s Overlook hike
• Sunday: Tubing at Butternut in the morning, Bullard Woods hike in the afternoon
• Monday: Monument Mountain hike, visit with Nana and Papa, Baba Louie’s takeout dinner
• Tuesday: School/work/play in the morning, sledding with Papa in the afternoon at the Stockbridge Bowl Beach hill.  I took the day off and escaped for a solo hike at Bartholomew’s Cobble while everyone was working in the morning - best decision I've made all year!  Four hours of alone time!
• Wednesday: School/work/Inauguration Day excitement in the morning, visit with Gammy and Riri, No. 6 Depot takeout lunch, Pleasant Valley hike in the afternoon
• Thursday: School/work in the morning, skiing in the afternoon
• Friday: School/work in the morning, Tyringham Cobble hike in the afternoon, Betty’s Pizza Shack takeout dinner
• Saturday: Bartholomew’s Cobble hike in the morning, Erin and I did the Housatonic Flats loop in the afternoon, Mexican takeout for dinner from Xicohtencatl
• Sunday: Housatonic Flats loop in the morning, No. 6 Depot takeout breakfast for the ride home

Hiking
Most of our activities were hikes. Just this year, with Henry in kindergarten, we’ve been able to start doing “real” hikes as a family. We still max out around 3 miles in distance, and always come armed with a backpack full of snacks and an expectation for some whining, but we generally find that everyone is happy and proud of themselves at the end, even if there is resistance to setting out or complaining along the way.

We are members of both Mass Audubon and The Trustees so we brought our member handbooks for both, which provided a nice hands-on way to read about their different properties and choose our adventures - all of the same information is available online, too. We also hit a few local properties run by the Berkshire National Resources Council (BNRC). The maps at the trailheads were of varying quality, so we always tried to take a screenshot on our phones before we left home to make sure we had a clear picture with us. 

Olivia’s Overlook (BNRC)

• Stockbridge
• 2.2 miles
• 550 feet elevation gain
• 1.5 hours
• We did the Charcoal Trail.  It was much harder than we expected because of the hills and the snow!

Bullard Woods

• Stockbridge
• 1.9 miles
• 240 feet elevation gain
• 1.5 hours
• 1 geocache!
• Easy afternoon hike right in the neighborhood

Monument Mountain (Trustees)

• Great Barrington
• 3.5 miles
• 775 feet elevation gain
• 2 hrs 40 mins
• We took the Indian Monument Trail (blue) up for a more gradual ascent, snuck onto the Squaw Peak Trail (red) for views from the peak, and went down on the Hickey Trail (yellow).  It was very icy in many sections, so we did a lot of sitting down and sliding!

Pleasant Valley Wildlife Sanctuary (Mass Audobon)

• Lenox
• 1.25 miles
• 157 feet elevation gain
• 1 hour
• 1 geocache!
• We took the All Persons Trail to Pike's Pond Trail to Yokun Trail and back on Bluebird Trail.

Tyringham Cobble (Trustees)

• Tyringham
• 2.27 miles
• 483 feet elevation gain
• 1.5 hours
• We did the Loop Trail, with a section of the Appalachian Trail!

Bartholomew’s Cobble (Trustees)

• Sheffield
• 3.1 miles
• 600 feet elevation gain
• 2 hrs 15 mins
• We took Ledges Trail to the Tractor Path, up to the top of Hurlburt's Hill.  We made our way down on Tulip Tree Trail, Boulder Trail, and Bailey Trail, back to Ledges Trail at the beginning.  Amazing views at the top of the hill and lots of fun trees to climb and streams to cross in the woods!

Housatonic Flats (BNRC)

• Great Barrington
• 1 mile
• No elevation gain
• 30 minutes
• 4 geocaches!
• Easy all-persons loop 

Snow Sports
We went to Ski Butternut twice, once for tubing and once for skiing. I was a little nervous about crowds, but we felt very safe both times.

• Tubing is available on weekends/holidays only, so we made a reservation for the first slot on Sunday morning (10am-12pm). It was more crowded we expected when we pulled in, but you’re naturally social distanced based on the size of the snow tubes and masks are strictly enforced so we never felt uncomfortable. You check in for your reservation at a little booth outside.

• We went skiing on a Thursday afternoon and it was very empty. We signed the big kids up for a First Timer Package with a 2-hour lesson and rentals, and the three of them were the only ones in the group, along with two instructors. They are strict on the age 6 minimum because the instructors aren’t allowed to help the kids up this year, so Zach and I just bought afternoon passes/rentals for ourselves and Henry, and tagged along next to the kids’ lesson to pick up tips! The mountain is small and we stuck to the beginner area with two magic carpets, but it was perfect for our level of interest and experience.

Food
We did an Instacart delivery from Big Y on Saturday morning, and made two quick runs into Guido’s Market for some specialty items mid-week. We mostly cooked our meals at home, but did takeout a few times and found all of the restaurants to be well-equipped with Covid precautions.

• No. 6 Depot (West Stockbridge): the best coffee! We ordered breakfast/coffee twice and lunch once, and everything was always delicious. Online ordering/curbside pickup. 
• Baba Louie’s (Great Barrington): everyone said this was the best pizza in the area.  We thought it was pretty good - the kids' main criticism was that they don't have a plain cheese pizza, unless you count a Margharita pizza (and ours don't.). But the salads were enormous and they had lots of interesting pizza options. Online ordering/curbside pickup. 
• Betty’s Pizza Shack (Lenox): the kids gave this 5 stars and we really liked it too. The small pizzas were almost as big as the large. Phone ordering/cash only.   
• Xicohtencatl Mexican (Great Barrington): yummy, big portions - we split 3 entrees and 2 appetizers (and supplemented with mac and cheese at home). Phone ordering/inside pickup. 

Shopping
I love a good local shopping trip on vacation and really miss the luxury of perusing stores. I did pop into Shaker Mill Books and the Country Store in Stockbridge, and What a Gift in Lenox. They all mandated use of hand sanitizer at the door and had a limit on the number of customers in the store, and except for the Country Store, I was the only person in each shop the entire time. 

We crammed a lot into our week+ away, and accomplished almost 25 hours toward our #1000hoursoutside challenge even while balancing remote work/school most mornings.  We balanced all that out with lots of hot chocolate, card games, and Netflix in the king sized bed every evening, to make sure that we all felt like we were on vacation!  The change of scenery was good for everyone's spirits, and the kids gave the trip 5 stars in our debrief when we got home.  The Berkshires was definitely a great choice for a winter getaway, and we look forward to returning again to explore it in a warmer season!

Winter Getaway Packing

The nice thing about packing in a pandemic is that you know you aren't going to see anyone or go anywhere that requires dressing up! The forecast called for cold temperatures so we made sure we had lots of warm layers and comfortable clothes since we knew we'd be doing a lot of outdoor adventuring. We had laundry in the house and it was helpful for washing clothes mid-week for clothes, but was even handier for throwing wet snow gear into the dryer almost every night.

I typically give the kids a packing list about a week before we leave on a trip. I write it on a post-it note and stick it to the wall in the hallway outside of their bedrooms. They usually take a first stab at packing, and then I edit a day or two before we leave. They each pack their own suitcase, and we used a reusable grocery bag for each person's winter gear, which was super helpful for keeping it sorted both while we were packing and while we were away.

And of course, the sourdough starter, two fresh loaves of bread, and my birthday flowers made the trip - precious cargo in the front seat!

Here's what we brought:

Boys:

• 2 PJs
• 5 underwear, 3 wool socks, 2 regular socks
• 3 long underwear sets
• 5 pants
• 5 shirts
• 3 sweatshirts
• Sneakers

Girls:

• Same, with 2 fleece leggings in place of 1 long underwear and 1 pants

Adults:

• Same as kids, with 2 pairs of jeans and a few Zoom-appropriate tops

Winter Gear:

• Hiking boots (Mom and Dad), Uggs (Mom)
• Snow boots (all)
• Snow pants - we wore these almost every day for hikes and snow play
• Gloves/mittens - 2 or 3 pairs each
• Hats - 2 each
• Balaclavas - great for warmth and built-in masks
• Masks
• Hand/toe warmers
• Boot dryer - best purchase of the winter!
• Sunglasses
• Flashlights - fun (and helpful!) on late afternoon hikes
• Hiking backpack - we have a lightweight drawstring backpack that we use
• Water bottles
• Sleds
• We had planned to bring snowshoes, but there wasn't enough snow on the ground so we left them home

In hindsight, our packing list was pretty accurate.

• We never wore our sneakers because we basically lived in boots.
• We wore our snow pants almost every day to keep us warm, even on all of our hikes. I am confident that I wore my snow pants more in this one week than cumulatively over the past 5 years! 
• We Amazon Prime'd two extra pairs of kid mittens to the house because we found we were using multiple pairs a day and couldn't keep up with drying them! 
• We could have cut down the pants/shirts/sweatshirts by one, but were glad to have the variety.
• We lost one mitten and one balaclava somewhere in the house over the course of the week. Ce la vie...

How We Search for Vacation Rentals

Traveling with a family of six, it almost always makes more sense to rent a house than to stay in hotels. We love being able to cook meals at home and have space to spread out. Especially in the pandemic where we're not comfortable going into hotels or restaurants, vacation rental homes are a great option. Even before the pandemic, we had used these sites for many years for our summer Narragansett rentals, as well as for our trip to Quebec City last year.

We’ve had good luck with both AirBnB and VRBO in the past, and generally use whichever site has the house that is the best fit for our trip. There tends to be a lot of overlap between the two sites, but it’s not 100% so it’s worth checking both.

Here's how we approach looking for a vacation rental: 

• First, I look at location. I prefer to search in the “map view”, and zoom out to a pretty wide circle around the general area we’re headed to. It’s a good way to see the variation in price across different towns/neighborhoods, and get a sense of what’s available.  For our winter getaway during the pandemic, an in-town location wasn't important to us, but we wanted a large yard for the kids to play in when they finished school each afternoon.

• Next, I set our number of guests and minimum number of bedrooms. We can get away with three bedrooms for a weekend trip, but prefer a minimum of four bedrooms for longer trips, especially when we’ll be working/learning remotely.

• Some house listings include floor plans, which is helpful for getting a sense of layout.  The house we rented in the Berkshires had two bedrooms downstairs and two bedrooms upstairs, which is not our ideal configuration with four kids, but it was helpful knowing that ahead of time so we could start managing expectations with the kids about who would sleep where!  

• I always filter down to houses that have good reviews (4.5 or 5 stars) from prior renters. Reading the comments/reviews is super helpful. The house we rented in the Berkshires had a few reviews from other families who had visited during the quarantine and it was reassuring to read their comments about the strong WiFi and Covid safety protocols. 

• Laundry.  Always make sure there is laundry!  We somehow overlooked this key detail when we rented on the Cape last summer and will never make that mistake again!  

• Always check the cancellation policy - I’ve been surprised at how different the cancellation policies are for different houses. Some of them have no cancellation flexibility, and others offer cancellation up to the week of your trip.

Happy traveling!