To the Berkshires & Boston
I know super cheesy headline, but with fall that's just our drift. Perhaps a bit of an older crowd adventure we're avid Leaf Peepers. New England has to be one of our favorite places in the world during autumn. It's scenic colors, atmosphere and spooky vibe are literally almost unmatchable. Summer vacations have never really been our thing. Our yearly trip is all about getting spooky with fall.
This 2020 we hit the road with the huskies headed to New England. Our coven command center is in Chicago so this is no little road trip for the faint at heart. At a minimum the trip is 15 hours without stops. So imagining packing two people and two large huskies with fill ups, doggy breaks, and stretching your legs it's quite the journey. The previous year in 2019 we hit the road to Salem so this wasn't our first time making the journey. Having gone to Massachusetts before this helped us know the expectations of the trip. Going there we decided to not make any sightseeing stops and wanted to go the fastest route possible. We planned the journey to stop in Connecticut overnight in a hotel then head onto Boston.
Our plan was to drive up into western Massachusetts into the Berkshires and then east on the Mohawk Trail. Listed as one of the most scenic byways in Massachusetts especially during the Fall it was a must see. Starting out as a Native American trail in northwestern Massachusetts, its now known as route 2 and 2a. The views of the Berkshires, the winding road, gift/antique shops and small beautiful towns make it a gorgeous drive. The historic French King Bridge's view at 140 ft up through the region makes the drive alone worth the time. We made several stops for pictures, meandered through-out the morning in small idyllic towns loving the fall atmosphere. We couldn't recommend it enough and definitely will be going back for another drive for more adventures. Sadly we were a bit early for some of the trees as they hadn't turned yet but still the views were spectacular! After heading closer to the coast we decided to stop at several Apple Orchards along our route. If anything while leaf peeping, apple cider and cider donuts are a must. Our adventure took us to Shelburne Farm, Carver Hill Farm, and Honey Pot Hill Orchard. Each are fabulous, fun and full of fall vibes and we can't possibly choose one over another. We recommend googling each if you must pick just one. Your waistline might not love you but your tastebuds will adore you with every cider filled bite.
Continuing our journey, we booked an Air BnB outside Boston for our first three days of our trip. We decided as a home base it would work to travel from the hotel in Connecticut through the Mohawk Trail, then onto Salem, also for a day trip to Maine and into Boston perfectly rather than choosing a single place. Location is key really and getting the most out of the area during our stay and this location worked wonders.
For any Halloween lovers next to New Orleans, Salem Massachusetts is a pilgrimage each enthusiast must travel to at least once in their life. It's an adorable town with all the Halloween vibes that yes might have a dark past but has made the most of it's history. As with any town that seeks attraction it does have some serious tourist traps and crowds. Salem in October is mad with people, vendors and fest's for the ghouls at heart.
We didn't mind but some others might not. So why Salem for us? As Halloween lovers in our spooky hearts we have some serious love of Hocus Pocus. Yes we're aware the entire film wasn't filmed in Salem, yes we know the Sanderson sisters aren't real, but we couldn't care less. The town does have many tours available, catering to all enthusiasts (history, movies, ghosts, etc). They're available to tour for whatever has bewitched your interest in Salem. It's always a good start if it's your first trip to book a tour. Having our Huskies with us it does complicate the tour selection but some outdoor walking tours do allow dogs and calling ahead and asking is always a good idea we've found. If your not the tour type we found you can follow a brightly marked red line around the town hitting all the historic spots on your own. It's a bit long walk but it does make for a great guide less adventure for those who are up for it. With Covid we stopped in Salem, Sunday morning bright and early to avoid people. Taking in the Salem Common, Rope Mansion (Allison's house), Rope gardens, graveyards and followed the brightly drawn red line around town.
After taking in the witch capital, we headed onto Kennebunkport, Maine through Gloucester. If you haven't realized yet, we're very overzealous road trippers who love to take in as much as we can in whatever area we've traveled to. Gloucester Massachusetts is a costal town full of fishing history. Upon driving into the town a fisherman statue has
been dedicated to the lost sailors at sea, is beautifully placed and a mournful statue all at once. We stopped for lunch at the Blue Collar Lobster making the most of being seaside before we headed onward in our journey. The food and views were more than we bargained for, for a lunch time stop.
Prior to our trip, we read that Kennebunkport was one of New England's most scenic and idyllic towns which sold us on making the short day trip to explore. The drive up from Gloucester, Ma takes about hour and a half. Being a costal town filled with antiques, small shops, and packed of New England charm we fell in love with it immediately. It's a weekend getaway town that is food for your soul and we're not even talking about the food. Parking and exploring the town and staying a few hours or the weekend is highly recommended.
After exploring we ate dinner at the adorable Batson River Brewing & Distillery al fresco that's also dog friendly (a huge plus for us). Excellently paring food with beers and spirits their gastropub is a great way to unwind from exploring Kennebunkport and breathing in the fresh fall air while you relax next to warm fire.
Our trip to New England wouldn't be complete without a stop in Boston. This wasn't our first time visiting so we didn't do the full tourist shenanigans in the town. Taking the huskies on a nice walk in the Common was on our list as it's one of most beautiful places in the city to roam and enjoy outside. The garden and walkways are beautifully done with historic tidbits that we loved to stop and take in on our walk. We then meandered into Beacon Hill and of course made a stop at the Instagram-able Acorn St. taking a few shots for the gram too.
Beacon Hill is an adorable neighborhood worth exploring on foot to take in. This was our final stop in the Massachusetts road trip. Our next leg of our fall trip journey's to the island costal life coming in another post soon!
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