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Lexington Massachusetts Road Trip Guide

Lexington Massachusetts Road Trip Guide - Simply by Simone in front of the Inn at Hastings Park

Around three and a half hours northeast of Westchester County you’ll find Lexington, Massachusetts. Both quaint and historic, it’s where the first shot of the American Revolutionary War was fired, Lexington is on the perfect path for your next road trip this Summer.

Where to Stay in Lexington Massachusetts

I was so excited to stay at the Inn at Hastings Park again. This time with my good friend Jackie Giardina blogger from livingaftermidnite.com. First, feel instantly at home here. If home was a modern yet historic abode nestled in New England. After parking your car in the hotel lot you walk into a beautiful green and black cameo print wallpaper and a grand wooden banister leading upstairs to the Main House guest rooms.

The last time I came, we stayed in the Main House in a Superior Room. It was the perfect amount of space, equipped with the cutest smeg refrigerator and a fireplace.

This time around we are staying in the Barn Suite. And fun fact, this once was an actual barn used as a carpentry shop by its earliest inhabitant, Isaac Mulliken. This suite offers a king-size bed, pull-out couch, sitting nook, fireplace, and a full-size soaking tub in a bathroom.

Entry way at the Inn at Hastings Park in Lexington Massachusetts
Simply by Simone and Jackie Giardina at the Inn at Hastings Park having Coffee in bed

The Culinary Garden featuring Whispering Angel

The best part about staying at the Inn at Hastings Park is the culinary garden. You can book your stay and have it planned around an immersive culinary experience that includes history, wine pairing, and culinary instruction from owner, Trisha Pérez Kennealy (@trishaperezkennealy). After your first interaction with Trisha, you’ll also gain a lifelong friend.

During this particular stay, the @innhastingspark launched its Summer pairing menu. Each course is paired with the perfect rosé – my favorite was the sea scallop with lemon sauce. But the pork tenderloin with the Garrus Rosé was a close second. And that’s just one small part of the entire culinary experience. Last time we did the cooking class which I covered as well.

The Whispering Angel Culinary Garden at the Inn at Hastings Park
The Whispering Angel Culinary Garden at the Inn at Hastings Park Pairing Dining Setup
Simply by Simone sitting at dinner at the Inn at Hastings Park Whispering Angel Culinary Garden

What to Do in Lexington Massachusetts

Get Active. Take a jog from the Inn at Hastings Park through town. Or better yet borrow one of the Inn’s bikes and take a ride down Minuteman Bikeway. We didn’t do this on our trip since we were only in Lexington for 24 hours but it’s on my list for next time!

Shopping. Fancy Flea Antiques & Fine Jewelry is right in the heart of town and I highly recommend stopping in. They have a large assortment of estate jewelry you won’t want to miss. There’s also the Crafty Yankee and Michelson Shoes. And ten minutes down the road in Burlington is a huge mall that includes stores like Nordstrom, Arhaus, Madewell, and Anthropologie.

Food. We had a great lunch at Tavern in the Square in Burlington near the mall. They make their own spiked seltzers and if you’re with a few people you can get a cocktail tower! We really wanted to try Row 34 but they weren’t open for lunch, if you like seafood I would definitely check this spot out!

Landmarks. Tours and museums located mere footsteps from the Lexington Battle Green, where the American Revolutionary War began. The Liberty Ride includes a trolley tour of the many historic sites in the area, such as famous taverns and battlefields.

Lexington Massachusetts Clock in Town Square
Lunch at Tavern in the Square

On the Road Lexington Massachusetts Road Trip Guide

We decided to arrive in Lexington early on day one to explore the area there. But on our way home, we decided to stop in Sturbridge, Massachusetts which was about an hour into our trip home. I first found Sturbridge Antiques on my way to New Hampshire last fall and I’ve been dying to go back ever since.

I picked up three new vintage bags and an old blue glass medicine bottle. There are over 80 antique dealers so make sure you leave some time to get a good look at everything!

We had lunch at Cedar Street Grille — we both opted for salads and got onion strings and hummus for appetizers. The onions tasted like homemade funyuns and there’s a chance I’ll be dreaming of these forever! Overall a great little spot to eat!

Jackie and I wanted to take one last photo of our outfits and we found a cute spot where you could access Cedar Pond – just put the Sturbridge Host Hotel & Conference Center into your GPS!

Sturbridge Antique Center
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Final Thoughts

I highly recommend staying for an entire weekend so you can see all Lexington has to offer! I would even go as far as staying three days. The Inn at Hastings Park would also be a perfect anniversary trip for two if you book the culinary experience with your stay. I’ll definitely be back! Feel free to drop any questions in the comments!

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