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7 Best blogs and resources to plan your trip to the Berkshires (2023)

berskhires - autumn

The Berkshires have a long history of being an escape to the country from the city, particularly for people coming from New York and Boston. If it’s your first time or your 100th time to the region in Western Massachusetts, we wanted to pull together some resources to help you plan your next trip. 


Designed to spur economic development and tourism to the region, has all types of resources whether you’re looking to live, work, or visit, the team provides a wealth of knowledge on all things Western Massachusetts. Their helpful “Plan Your Trip” section has ideas for how to spend your weekend, how to get around, and events scattered throughout the region. This is a great starting place for anyone planning a trip to the Berkshires. 


Managed by a team of locals to the region, is a one-stop shop for anything you may need during your trip to the Berkshires. The writers curate everything from performing art schedules, to fishing recommendations, restaurants, and event venues. If you’re planning a trip to the region, keeps a list of upcoming events that may be relevant for your vacation! 

3. New England with Love

Amy writes about all things New England on her blog and it’s an extensive resource for some of the most gorgeous towns and cities from Maine to Connecticut. On her blog, she has a comprehensive guide on what to do in the Berkshires and even breaks down some of the best activities from skiing to staying cozy by the fire during the winter. Definitely bookmark New England With Love for your next trip to the Berkshires or really anywhere in New England! 

4. Eater

Everyone loves a good list! Eater has you covered with their list of best restaurants to eat at in the Berkshires. The region is home to incredible coffee shops, sustainable farm-to-table restaurants, and nearly every type of cuisine you can imagine and Eater does a pretty good job of sharing some local favorites. 

5. Berkshire Natural Resources Council

One of the main reasons people come to the Berkshires is to eat delicious food and get outdoors! The Berkshire Natural Resources Council’s mission is to preserve land across the Berkshires to ensure it remains beautiful. In addition to their important mission they also have helpful resources on popular hiking trails. You can also check out the list of some of our favorite hikes in the Berkshires that we curated for guests staying at Oak Hill House. 


This boutique hotel in North Adams has become a go-to gathering place for locals and visitors to the Berkshires. The Airport Rooms, their cocktail bar and restaurant, serves up craft cocktails and tasty treats that are great after a long summer hike or to cozy up by the fire on those bitter cold winter nights. They keep a list of art and adventure experiences updated by season, with everything from trivia night to a guided snowshoe adventure. 

7. Travel & Leisure

The popular travel site covers every nook and cranny of the word, but their writers seem to enjoy themselves when they visit the Berkshires. In the past, they’ve talked about what’s new in the region (2022) and some of their favorite things to do in the region (2022) that can provide a great framework for an itinerary for your next visit. They cover everything from great restaurants, scenic adventures, popular cultural experiences that will make a nice, well rounded trip for any traveler! 

Recap: Top blogs and resources about the Berkshires for planning a trip in 2023

Whether you’ve never visited the Berkshires or visit every year, there are plenty of resources to help you plan your next trip to the Berkshires, one of the most beautiful regions in the country! Given its proximity to New York and Boston (only 2.5 hours!), this is a great place to visit year after year and during different seasons to immerse yourself in the arts, culture, food, and outdoors.