Weekender's Guide - Winter in the Berkshires

There's something about a mountain town in the winter. Cozy restaurants, Adirondack chairs around a fire pit at a lodge, family-friendly ski mountains, a classic diner, and decorated Main Streets. Vermont, New York, Maine, and New Hampshire offer some of these quintessential and oh-so-nostalgic mountain towns. They do, however, come with a longer travel time and higher cost.

A solution for the coastal Connecticuters who want a more budget-friendly option that is also a little closer to home? The Berkshires. The Berkshires are a section of Western Massachusetts where the Vermont-based Green Mountains spill into the Bay State.

The largest municipalities associated with the Berkshires cultural region include Pittsfield, North Adams, Great Barrington, Williamstown, Stockbridge, Lee, and Lenox. The highlands of Massachusetts don't boast towering jagged peaks but instead, host smaller peaks ranging from about 700 to 1,200 feet. The area is home to a few different ski resorts, Butternut, Berkshire East and Jiminy Peak being the most well-known. The mountain towns on a small scale which generally means easy access, less crowded, and more affordable options.

Couples trip, girls weekend, solo exploring, a long day trip, or a weekend away with the family. If you want to explore mountain towns in the winter, the Berkshires are a great option.

Winter Lights at Naumkeag in the Berkshires (Stockbridge, MA)

 

The month of December is when tiny towns across New England turn into a Hallmark movie. The coffee shops and storefronts are decorated with lights and garlands. Carolers sing through the firelit dining room of historic restaurants. Tree lightings and winter festivals bring in the crowds while light parades close down wreath-lined Main Streets. Holiday events take over our weekend calendars and we all bundle up to sip cocoa and enjoy the season.

Stockbridge, a small town home to Norman Rockwell in the Berkshire Mountains of Massachusetts, does all of this with a heightened level of charm. Not only do they turn their town into a snowglobe backdrop, but they offer one of the best light shows in the country. Winterlights at Naumkeag offer a magical outdoor holiday experience at the famous estate which is a New England holiday event that cannot be missed. 

Laura's Tower & Ice Glen Trail (Berkshires) Stockbridge, Massachusetts

New England will never cease to amaze me with all of its beautiful nooks and crannies. This was another one of those "rain came in we need to pivot" situations. We left the Catskills, stopped for coffee and a walk-in Hudson, and stopped again in the Berkshires (Stockbridge, Massachusettes) to be exact.

I quickly looked up hikes in the area, on the hunt for something under 5-miles with the baby and the dogs. Laura's Tower had some great reviews and the pictures offered a lookout tower that offered sweeping views of the Berkshires. I read a little further and someone suggested the Ice Glen Trail in addition to the trek to the fire tower. 

The best part about this hike (and the big sell for me)? It's only 5 minutes from downtown Stockbridge which is an amazing little town that's getting its own blog post. Pair this hike with lunch downtown and if you have the time, an overnight stay in Stockbridge. New England small town perfection.

Laura's Lookout Tower

A Day Trip to Martha's Vineyard

Towards the end of a cold New England winter, and about the time I met Adam, I started putting together a New England summer "sorta bucket list".  It's a list of all the things and places I wanted to see in the near future. My list was places suggested by a friend or gems I found online that I quickly jotted down in a spreadsheet before it was lost in my brain, drifting somewhere between the never-ending To Do List and much-needed Grocery List. But because this is 2019 and I almost always have a computer in front of me or a phone nearby, this list turned into one long google doc I can add to wherever whenever.  

Scuba Diving with Seals - Glouchester, Massachusetts

Diving in New England gets a bad rap.  It's murky, it's dark, there is nothing to see, the water is cold.... Oh, the list goes on.  For all the warm water divers out there, who only don their gear when the temperatures are warm and the water is clear, you are missing out on some amazing local diving.  Amazing sea life, famous ship wrecks, and artifact finding right here in our sometimes murky waters.  

If you are lucky, you may even get the chance to swim with something a little bigger than lobsters and flounder.  Over labor day weekend, I had this awesome opportunity to spend some time in the water with some of New England's favorite residents, harbor seals and gray seals. 

1 Hike 2 Breweries- Easthampton, Massachusetts

There are very few things better than scouting out a new brewery after a hot New England hike.  The temperatures were in the 80s in September and after a lovely hike up to the summit of Mount Tom, I was happy to discover that there were two breweries just a few miles away. New City Brewery and the Abandoned Building Brewery were both in the same complex a 5 minute drive from the state park entrance.  With Olive in tow, we headed out to try some local Massachusetts beer.  

Hiking Mount Tom - Holyoke, Massachusetts

Hiking in New England can be a battle.  Sometimes (okay, often) you have to travel to find a hike with some elevation and scenic views.  Getting above the tree line and a view besides a forest of oaks can often be tricky.  Located about an hour and a half from home, this hike was a relatively easy drive and day trip for a great workout, beautiful views, and a chance to take Olive out on a hike. Dog-friendly, a ton of local breweries, and easy access and from what I hear one of the best day hikes in Massachusetts. Let's talk Mount Tom. 

Diving Back Beach - Rockport, Massachusetts

Back beach, Rockport

If you missed Monday's post, I talked all about New England diving and our first dive site on Sunday morning, Folly Cove.  After a great dive at Folly Cove and a quick surface interval, we made our way back to the cove (without our gear) to see how the entry would be as the tide receded.  They were NOT kidding about that dive site at low tide, its nearly impossible to get across those slippery rocks with heavy gear.  

After the tide was too low and the rocks FAR too slippery for a second dive at Folly Cove, I headed south to Back Beach in Rockport, Massachusetts with fellow divers Corey, Emily, and Chris. 

Diving Folly Cove- Gloucester, Massachusetts

New England diving usually goes a little something like this.... Rocky shores, zero to there-are-my-dive-buddies visibility (10 feet?), and marine life typical of the Atlantic shores ranging from a hue of brown to brown.  It isn't always the most exciting of marine life or best visibility, but I will say this without a doubt, it makes you a better diver.  We are all used to "brail diving" as we like to call it, when the visibility is so bad you just sort of feel around with your hands to find the bottom or things around you so when things get mucked up or the vis is low, we don't panic. 

Before I go on, know I am not complaining, that diving these sometimes murky Atlantic waters is how I love to spend a Wednesday afternoon (and many a weekend).  You should also know not all New England waters are treated the same.  Where Stonington Point usually sees visibility in the 5-10' range, many lakes, quarries, and areas of our coast get visibility ranging from 20 to 30+' which to us New Englanders is amazing.  We can travel around the NE coast to find some better visibility and abundance of critters.

Following Boston's Historic Freedom Trail

To say things have been a little busy over at KW would be an understatement.  Horse races, trips to Newport, some scuba diving and of course, the typical work grind has been dominating my schedule.  Thanks for your patience as we (slowly) recap the last few weeks of wanderings and more specifically, showing off New England to Amanda.  

Amanda was flying into Boston with an arrival time of 6:30am in the beautiful city of Boston.  The sun was shining, it only took me 1.5 hours to get to Logan Airport, we had just arrived at the Boston Commons, the clock read 6:50 am and there was absolutely no one in Boston.  We parked the car by Boston Commons (free parking on Sundays!) and headed to the Thinking Cup for breakfast.  I grabbed smoked salmon on a bagel and a coffee and we headed out of the shop and on our way to the days scheduled activity:  walking the Freedom Trail, Boston's most popular attraction.

The Freedom Trail is something most New Englanders do at least once on a field trip as a small child.  It is not something you look forward to (i.e. a whole day of walking looking at historical sites you do not give a hoot about at that time in your life).  For me, the only things I could remember was the 2 billion stairs to a tower and Mother Goose's grave (it's a thing).  What can I say, I was an attentive adolescent.

I was really excited to spend the day in Boston, walking along the Freedom Trail and soaking up Boston's History- this time for keeps.  About 20 years later, something I had dreaded on a day long field trip was now something I was waking up at the crack of dawn on a Sunday to do.

Hiking the Seven Sisters- Mount Holyoke Range, Massachusetts

I spent the month of November in a hiking rut and I needed to switch up my routine.  I needed some elevation, sunshine, and vistas in a new town to kick off the sunny November weekend.  

I wanted to stick to a 2-hour radius of home that way I could for-go hotels and keep it a day trip.  So on my quest for a new hike I did what any last-minute-lazy-hiker does: I hit google maps to do a little research and see what I could find.  Pretty soon, I stumbled upon the ridge walk among the Seven Sisters across the Holyoke Range in Western Massachusetts, a hike that appeared to be exactly what I was looking for.  Elevation, a good workout, vistas, summits, historical hotels and an overall great hike in a really fun town.  The hike itself was a treat and the college town of Amherst with its breweries and restaurants was an added bonus. Hike, a new town to explore and a few breweries? That is the Katie Wanders Way 


We jumped in the car and drove the two hours across the state of Connecticut and into Massachusetts to start our hike in Amherst. The plan was to follow the 6 mile hike along the ridge of the Mount Holyoke Range, following the Metacomet-Monadnock Trail (a section of the New England Trail) across 10 peaks, to the Summit House and end at another trailhead on Mountain Road. If we were feeling really adventurous we could retrace our steps back across the 10 summits (as the famous trail race does) or the more practical option: call an Uber which would take us the 6 miles back to our car at the opposite trailhead ($8, 10 minute ride).  And yes, we are practical (and sometimes lazy) hikers.  

Hiking Mt. Greylock - Massachusetts' tallest peak

On a whim, I decided to make September "Hike all the New England Peaks Month". When the temperatures started to drop and the bugs were gone, I headed to the mountains. Hiking hiatus is over. The first weekend of September brought my first New England hike to Connecticut's tallest mountain summit, Bear Mountain at 2,323'. The second hike (why you are here today) is to the summit of Mt. Greylock, Massachusetts's tallest peak at 3,491'. And this weekend, it was the grand slam, up to Mt. Washington, New Hampshire's tallest peak. The only three peaks remaining are Vermont and Maine, oh and the hill in Rhode Island. 

But back to Massachusetts.

Farm at the Hopper Road Trailhead 

We really enjoyed this hike. It was a great loop hike around the mountain starting at an old farm. The materials (directions, maps, etc) available for the hike were great, online and at the trailhead. The trail had a lot of signage, but there were a lot of different trails weaving throughout the forest (pay attention to trail signs).

This was a great way to hike a portion of the AT, see a few waterfalls, hike along a river, stop at a few summits, and stop at the main summit. I loved the scenic overlook at Stone Ledge Vista. The hike was steep in parts and humid, but overall the elevation was spread out well over the distance. We had a great lunch at the summit and refilled our water, although we had absolutely no views with the clouds and fog. We continued on the loop hike but by mile 11 we were a little over the hike and ready to be done. The last two miles down Haley Farm Trail were steep, and felt like they took forever. Overall, the trail was beautiful and we were glad to bag another peak, the highest in MA.

Camping at Pittsfield State Forest - Massachusetts

On a whim I decided to make September "Hike all the New England Peaks Month".   I mean, we are talking really unofficial here but when the temperatures started to drop and the bugs were gone, I headed to the mountains.

My first hike was to Connecticut's tallest mountain summit, Bear Mountain

And my second hike the following weekend up Mt. Greylock, Massachusetts' tallest peak.

And next week, it's the grand slam, up to Mt. Washington, New Hampshires tallest peak.

Three New England peaks in 3 weekends.  Vermont and Maine, I am coming for you if time allows. But back to Massachusetts.

I woke up early Friday morning (6am to be exact) just to pack my car with the needed supplies for the weekend.  Everything for camping from tents to the charcoal chimney, hiking, food for the trip, and whatever the dog needed (if you have ever been camping you know its a process).  The plan was to meet Thatcher after work in Old Lyme and head north up Route Nine to Pittsfield Massachusetts.  I chose Pittsfield as our stop because at just 20 minutes south of the mountain, it was a great place to camp before hiking in the morning.  Things got a little chaotic when Thatcher showed up without his sneakers and I refused to let him return home to get his shoes and back which would put us at 1:20 out of the way to Stonington and back (without bad traffic).  A trip to Dicks Sporting Goods and chick-fil-a solved the sneaker issue and the bad mood.  Thatcher is the proud owner of a new pair of Merrills.  

With the delays, we arrived at Pittsfield State Park at about 9 pm, of course after the sun had set.  We found the park without an issue, and arrived at the front desk to check in.  The staff is there until 10pm and there were plenty of sites available when we checked in.