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.

Weekender's Guide to Charleston, South Carolina

Adam and I planned to spend our anniversary weekend up in the White Mountain of New Hampshire. I was excited to get away just the two of us in our camper, to go hike some of the bigger mountains without having to drag to kids along (literally). As our anniversary approached, the weather started to look like a complete washout for the weekend and we made the last minute decision to pivot. I quickly set out to Google Flights to see if I find an inexpensive deal out of our local airport (one terminal New Haven airport an easy 30 minutes from our house). We ended up paying $289 for both of us to fly round trip to Charleston, South Carolina and back. And the best part? We pulled into the airport at 5 and we were having dinner under the palm trees by 8pm. Parking and security is about a 2 minute process and flying from one small airport to another with very little driving on either end was a weekend warrior's dream.

***Charleston is typically serviced by a lot of these budget smaller airlines making it an EASY and AFFORDABLE destination

Weekender's Guide: Catskills, NY (Summer!)

The Catskills have become one of my favorite places and I never saw it coming. Meeting Adam who lived in Fairfield County (the insanely busy part of Connecticut that touches New York basically) sort of changed things, putting the Catskills that much closer.

In my Rhode Island Weekender's Guide, I talked about how Jamestown was like Newport in miniature. Well, the Catskills are that for the Adirondacks. The Catskills are a smaller less populated version and while you don't have the Adirondack High Peaks and famous lakes, you have some amazing hiking, stunning vistas and the scenic Esopus Creek. It's also a much easier drive as the Catskills are about 3.5 hours closer than the Adirondacks for us in coastal Connecticut, only 3ish hours from home. Adirondacks are beautiful but pretty far for just a weekend but the Catskills? You can leave on a Saturday morning if you wanted to avoid the traffic. The Catskills are a popular spot for city dwellers as it's also a 2 hour drive from New York City, making this the perfect weekend getaway for New Englanders and New Yorkers alike.

Weekender's Guide: Stowe, Vermont (summer edition)

Stowe is one of those four-season towns that New Englanders keep coming back to. There is something fun to do when the leaves change, when the snow falls, when the flowers bloom and when the summer sun is out. Stowe even made the cut on Travel & Leisure's 11 of the Best Small Towns in America and after a weekend in this mountain town, you will see why. I've been spending time here in the mountains with friends on a girl's getaway, a weekend ski trip with significant others, and now, a summer getaway with my little family and I promise, Stowe is worth the hype. 

Not only was this one of our first family getaways, but this was Adam's first time in northern Vermont (ever) which meant I had a jam-packed weekend planned - Katie Wanders style. I had a fun weekend planned and working around a 4-month old baby and our two dogs gave me a new perspective on travel as a family of 3+. Stowe is a great place to bring the kids and the dogs and we were so thankful for all the dog-friendly patios, budget-friendly lodging options, and opportunities to be outside with our sometimes fussy babe. 

Mount Hunger (nearby Waterbury, Vermont)

Stowe Recreation Path

There is something for everyone in this small mountain town. Active adventurer? There are a lot of great hiking and biking options. Relaxing foodie? You have so many options when it comes to breweries and restaurants and you can spend the weekend eating and drinking your way through town. Bringing the family? Take the kids to one of the swim holes, take a gondola ride up the mountain, and check out the miniature golf course. Whether you are heading up solo or traveling north with a little one or the family dog (or both), this guide is for you. 

Keep on scrolling to see an example of what our weekend in Stowe looked like. You can also make this a "Mix & Match" sort of guide by scrolling to the bottom and picking your kind of weekend from the Eat, Play, Hike, Drink categories at the bottom of the post. 

Weekender's Guide to Jamestown, Rhode Island

I love Jamestown 100 different ways. For many, it's the island between the bridges, the town next to Newport, the exit right before the tolls.  For me, it's all quiet roads and ocean views, historic lighthouses, and gorgeous parks. You can find quiet farms and historic forts, scuba diving spots, and seafood menus. Spend an afternoon in the cove watching sailboats float by, soak up the sun or go for a swim. When you want to get moving, jump in a kayak and drift with views of tall ships and beautiful bridges. If you prefer to stay dry, grab a bagel and a bike and cycle the island loop, challenging yourself over the rolling hills. If golf is how you prefer to move, play 9 holes on the local course - I hear the burger after hits the spot.