Weekend Trip: Wine, Beer, and Food in Hampshire County Massachusetts

When people think of Massachusetts, they usually think of Boston, the eastern epicenter of the state. But there’s an “other side” of Massachusetts that they’re missing out on: Hampshire County in Western Massachusetts.

A couple of weekends ago I had the opportunity to visit Hampshire County, Massachusetts with my boyfriend. We spent two days and one night exploring the towns of Northampton, Southampton, and Easthampton. Taking ourselves out of the guidebooks, we experienced Hampshire County the way that locals do and had a fun-filled weekend at the best wineries, breweries, and restaurants in the area.

Getting to Hampshire County, Massachusetts

Hampshire County is less than 2 hours from Boston. Just north of Springfield, it’s a quick and easy drive from Boston or NYC, making the area perfect for a weekend getaway. If you don’t have a car, the area is also accessible by bus, train, and air—Bradley International Airport is about a half hour away.

Small Oven Bakery Picnic Lunch at Black Birch Vineyard

We started our weekend off by picking up a picnic lunch at Small Oven Bakery, a quaint woman-owned bakery in Easthampton. Co-owners Amanda and Julie opened Small Oven Bakery just 2 years ago and have quickly become a local favorite.

We arrived at noon to a packed house and were greeted warmed by Julie who was packing up our lunch. While Julie prepped our lunch, my boyfriend and I chatted with Amanda for a few minutes over coffee about our love for all things bakery and small business related.

small oven bakery easthampton

With our picnic lunch packed, we hit the road and drove to the beautiful Black Birch Vineyard a few minutes down the road. The weather was perfect—warm and breezy with bright sunshine. Owner Mary Hamel greeted us and encouraged us to relax and enjoy our food on the picnic benches before our wine tasting.

black birch vineyard western massachusetts

The winery doesn’t serve food so visitors can bring their own to eat on the picnic benches and Adirondack chairs out back. The atmosphere is very relaxing and family friendly. Our fellow wine tasters included a family with a baby, a ladies birthday celebration, and a group of friend with dogs.

On a picnic bench overlooking the vines my boyfriend and I gobbled down our lunch from Small Oven Bakery—an open faced Roasted Cippollini and Radicchio baguette, a Boston Brisket sandwich, and a chocolate mint cake.

small oven bakery easthampton

After stuffing our faces, we headed into the winery, a converted barn with an authentic rustic feel. We tasted through, making sure to sip and dump because we were driving. Our favorites included the steel casked Chardonnay, Riesling, and 2013 Pinot Noir.

black birch winery western massachusetts

All of the wines were good but I was especially impressed by the Chardonnay, as I’m not usually a fan of the varietal. I enjoyed it so much I purchased two bottles to take home! Both Black Birch Vineyard and Small Oven Bakery were recently voted as The Valley Advocate’s Best of 2016.

black birch vineyard western massachusetts

Abandoned Building Brewery

We left Black Birch Vineyard and drove to Northampton where we were staying for the night so that we could drop off the car before heading to the breweries. Since we’re both big beer drinkers, my boyfriend and I called an Uber to take us safety to Abandoned Building Brewery, our next destination.

abandoned building brewery easthampton massachusetts

The aptly named Abandoned Building Brewery is situated in an abandoned building along the Easthampton Rail Trail. Windowless with swagged lights, mismatched couches, and board games, there’s a nostalgic feel to the brewery.  The comforting and homey space took me back to my high school college days of drinking in a friend’s basement.

abandoned building brewery craft beer flight

Kimaya, an staff member who has worked at the brewery since it opened, greeted us with two flights which we brought to the seating area. Seating is limited which encourages a communal experience with both the people and dogs visiting the brewery. We sat and chatted with some local residents while drinking our flights.

abandoned building brewery craft beer

While the company was great, the beer was even better! Brewer and owner Matt Tarlecki crafts the ales using hops from the brewery’s own hop field and malts from Massachusetts’s only malt house in nearby Hadley. My favorites were the Pennhurst Pale Ale and the Dirty Girl IPA and my boyfriend especially enjoyed the Nightshade Stout.

If you’re in town on May 7th, Abandoned Building Brewery is celebrating their second anniversary with live music, food trucks, and an outdoor beer garden—an event not to be missed!

New City Brewery

Our next stop was at the close by New City Brewery which sits literally next door to Abandoned Building Brewery. The breweries are next to each other along the Easthampton Rail Trail which makes for a comprehensive beer tasting bike ride. We saw quite a few cyclists who popped in for a pint with their pups. Although we don’t have a dog ourselves, we loved that so many places were dog friendly!

Open since 2013, New City Brewery is best known for its Jamaican style ginger beer crafted by brewmaster Sam Dibble but also offers regular beers. Devin, one of the four co-owners, welcomed us with open arms and two flights—one flight of New City’s beers and a second mimosa flight made with the ginger beer. As someone who loves ginger beer and mimosas, I was in heaven with the mimosa flight!

new city brewery western massachusetts

Like it’s next door neighbor, New City was hopping on the beautiful Saturday and appeared to be setting up for live music. With large windows, open space, and natural light, New City Brewery exudes a friendly hipster vibe—the good looking men behind the bar don’t hurt either.

new city brewery western massachusetts

Hotel Northampton

We caught an Uber back and checked into Hotel Northampton, our home for the night. Built in 1927, Hotel Northampton is a beautiful red brick building in the heart of town.

There was a platter of fresh fruit, cheese, and sparkling water waiting in our room when we arrived. A handwritten note and personal introduction from Ruby, the head of marketing and public relations for the hotel, made us feel very welcome.

hotel northampton massachusetts

Although historic with a traditional American feel, Hotel Northampton has the amenities and comforts of a modern hotel. Everything about the hotel was great—updated and spacious rooms with natural light, comfortable beds, a delicious breakfast, and free WiFi.

hotel northampton western massachusetts

Northampton Brewery

After a long day of visiting drinking establishments, we were more than ready for dinner at the Northampton Brewery. A quick walk from Hotel Northampton, the Northampton Brewery is New England’s oldest operating brewpub, serving up American style food and delicious beers.

northampton brewery western massachusetts

Like many small businesses in New England, Northampton Brewery was family owned and operated by siblings Janet and Peter Egelston and has ties to New Hampshire’s Portsmouth Brewery and Smuttynose Brewing Company. Not surprising, the beers were delicious! Along with nachos, a pulled pork sandwich, and pizza, my boyfriend and I enjoyed the Blue Boots IPA and Conundrum beers.

northampton brewery western massachusetts

Tunnel Bar

After dinner we checked out the infamous Tunnel Bar, voted by Buzzfeed as one of the top places to drink before you die. Tunnel Bar is a former train passenger tunnel from 1896, making for a cool underground experience.

tunnel bar northampton western massachusetts

Photo courtesy of Tunnel Bar

The long and narrow cocktail lounge was packed but the martinis were worth the wait.  It was a long day so after Tunnel Bar we retired to Hotel Northampton for some much needed rest.

Sylvester’s Restaurant

The next morning my boyfriend and I woke up refreshed and ravenous. We grabbed some coffee at the hotel and headed over to Sylvester’s Restaurant. Located in the house of Sylvester Graham, the inventor of the graham cracker, Sylvester’s Restaurant is a Northampton landmark and has been voted Best Breakfast and Brunch in Western Massachusetts for years.

sylvesters restaurant northampton massachusetts

We feasted on the Benedict Sly’s style, the banana Nutella French toast, and a homemade pop-tart style pastry that was to die for. Known for their eggs benedict dishes, the Sly style Benedict was delicious and almost more than I could eat. My boyfriend and I shared both dishes and still had leftovers to take home!

best brunch western massachusetts

Around Northampton

Stuffed from breakfast, we walked off our food around town. Home to Smith College and four others nearby, Northampton is a quintessential college town. Walking around instantly brought me back to my own college days in Madison, Wisconsin. Northampton reminded me a lot of Madison and I felt at home amongst the tall trees, beautiful buildings, hippie shops, and tiny cafés.

downtown northampton massachusetts

Aside from its college charm, Northampton boasts a small town vibe that makes you feel like you belong.  Everywhere we went, the people were friendly, welcoming, and excited to share their town with visitors.

Our weekend in Hampshire County was a wonderful break from the hustle of life and a good reminder that there’s more to Massachusetts than Boston. While the trip was full of adventure, there’s much more to explore and we can’t wait to go back to Hampshire County. If you’re looking for a romantic weekend away, a fun trip with friends, or a family-friendly place to explore, check out Hampshire County, the “other side of Massachusetts.”

Disclosure: This trip was hosted by the Hampshire County Regional Tourism Council and the local businesses mentioned in this post. Although sponsored, all opinions are my own.

8 thoughts on “Weekend Trip: Wine, Beer, and Food in Hampshire County Massachusetts

    • Emily says:

      Thanks for your comment Kristen! I’m glad you had as good of a time as we did at the breweries and commend you for riding bikes to and from them!

    • Emily says:

      Haha, thanks for your comment Tim. I’ll have to check out The Foundry the next time I’m in town. We were on a tight schedule in order to get in the other local favorites but this is now on my list. Thanks for the recommendation 🙂

  1. Shira says:

    Great choice of breweries! I drive a brewery tour bus, Ale Aboard, that goes to both those breweries and starts at Brew Practitioners. Next time you’re in town, you should take the bus instead of an Uber!

    • Emily says:

      Hi Shira – Thanks for your comment! I actually saw the Ale Aboard bus when we were walking to New City Brewery and took some information. What a great deal and an awesome itinerary and much more fun than an Uber! I’ll check it out for when we go back 🙂

  2. Danielle says:

    You’re reminding me I need a Northampton trip! I love it there. I was last out that way a couple of years ago and my mum and I ate at the Northampton Brewery on the back deck!

    • Emily says:

      Yes, it’s the perfect day or overnight trip! I imagine that it would be beautiful in the summer as well. I would definitely go back to try out more wineries and restaurants!

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