Maybe you recall my first trip to Woodstock two years ago. Since then I’ve always had a special place in my heart for this picturesque Vermont town. My mom turned 65 this fall and I thought Woodstock would be a beautiful place to celebrate her birthday, enjoy the foliage (duh) and have some great farm to table meals.During this trip there was a stop in Brattleboro along the way, which is about a 3 hour drive from NYC. It’s a great town for an evening out and some retro digs.

Downtown Brattleboro overlooking the Connecticut River

I’ve added a bunch of new go-to spots to my list and if you’re thinking about a trip there. If you’re looking to enjoy the town, some cheese tastings, vintage shopping and lots of fantastic food, I would highly recommend Vermont.

Stay

We arrived to Brattleboro on Friday afternoon and checked into the Latchis Hotel. This retro hotel is a converted movie theatre that still has a theatre on one side of the building (great for late night popcorn cravings!) The Art Deco rooms are clean, spacious and the beds and linens are incredibly comfortable.

An art deco hotel that offers a comfortable stay right in the heart of downtown Brattleboro

Eat

Downtown Brattleboro is only a few short blocks of shops and restaurants, a fun choice for a quick overnight in VT. We popped into duo for some wine and ended up staying for dinner, the great ambience and live jazz. A cozy American restaurant with a Mediterranean twist that’s the perfect place to linger from happy hour into your Friday evening. Snack on the house marinated olives with your wine. We’re still talking about how good they were.

Shop

Penelope Wurr is a gift shop owned and run by an English woman with the best taste in gifts from all over Europe. I got this wool German hat and I couldn’t be happier with the quality! Chic, non? I could’ve hung out there all night appreciating the greeting cards, art and holiday gifts! If you’re looking for something special for the holidays, check out her online shop here.

Check out Twice Upon a Time for vintage clothing, hats, home goods and loads of other fun stuff. 

*Still regretting that I didn’t get this hat

Before heading out of Brattleboro onto our next destination, we stopped at Grafton Village cheese shop for a tasting and an education on cheese. With a huge selection of fresh local cheeses as well as a variety from France and The Netherlands, there’s a cheese for everyone! 

My big takeaway was that the cheese is better here because of Vermont’s high mountains. In the summer months, the cows are moved to the top of the mountain where the grass is better and they are free to pasture. This explains why Swiss cheese is also so good! Don’t believe me? Check out this article. You’re welcome for the cheese lesson.

I was actually this excited when Phillip surprised us with this cheese stop before leaving town

My mom in her element

Brunch in Quechee

We drove about an hour north to kick the day off with a delicious brunch at Simon Pearce in Quechee, VT.  There’s a small bar area in the front of the store where you can enjoy beer flights and bar bites, like homemade kettle chips, while you wait for a table in the dining room.

The beer flight was the best deal $10 for 4 hearty tastings

Simon Pearce’s restaurant uses local ingredients serving delectable dishes like Vermont cheddar soup, beef stew, lamb burgers and other seasonal specialties.

The main floor offers a retail area that feels like some sort of glass museum with prices to match! Head downstairs to see glass blowers working at their craft.

View of the covered bridge and Ottauquechee River waterfall that powers the energy for the furnace that’s used to blow the glass.

Shop

A fun shopping experience in Quechee is the Antique Mall. It’s a huge antique store connected to several other gift shops and an Alpaca farm! You can buy scarves, hats and sweaters made from the wool of the Alpaca’s right outside.

This huge Antique Mall is a must visit in Quechee.

A Warm Woodstock Welcome

Staying at The Blue Horse Inn was one of my favorite parts of our trip.  The sweetest couple, Jill and Tony, just reopened this quaint Bed and Breakfast in the heart of Woodstock. They really nailed the cozy bed and breakfast feel that we were looking for. With a few sitting rooms each equipped with a fireplace to curl up with a glass of wine, cup of tea or a good book, this was one place I never wanted to leave.

We opted for the suite since there were 3 of us traveling. The king bed and linens are the most comfortable, there’s a brand new pullout bed that we were the first ones to sleep in!

Probably the most comfortable bed I’ve ever slept in

The breakfast was beyond delicious- homemade zucchini bread to start, a rolled cheddar omelet with spinach pastry or vegan granola cups with banana cream and berries served with green mountain smokehouse maple bacon village, sausage or vegan sausage from the Woodstock Farmer’s Market. It was heavenly.

Eat

There’s no shortage of good restaurants in Woodstock.

Mangalitsa. This will go down as one of my favorite dining experiences to date. Call at least one week in advance to reserve a table. A dimly lit, 20-seat dining space that offers a limited, yet delicious menu with a wide wine selection and the warmest service that makes you feel like you’re a guest in their own home.

The menu changes daily based on what is local and fresh. I had butter poached lobster.

Bentley’s

Serving up pub food and spiked apple cider, Bentley’s is the just the place for a hearty lunch, midday drink or even late night dancing (DJ on Friday and Saturday!)

Red Rooster in The Woodstock Inn

Located in the Woodstock Inn and Resort, this is a great choice for a bite at the bar or a nice sit down meal. Dine for breakfast, lunch or dinner. Don’t skip the bread basket! 

See and Do

Definitely make some time to walk around to see the beautiful landscape and covered bridges that are quintessential Vermont.

Visit the Woodstock Inn

Play pool, shuffleboard, pinball and life size scrabble

Curl up in front of one of the many cozy fireplaces.

Visit Sugar Bush Farm for cheese and maple syrup tastings. You can also feed the goats!

Unwind at the Spa

Cap off your weekend with a visit to the Spa at The Woodstock Inn. Book a service here and get access to the amenities for the entire day. My mom and I both had facials and we were so pleased with the service.

Enjoy aromatherapy in the sauna, multiple relaxation rooms, herbal tea and healthy snacks and Naturopathica products.

You can also order lunch and enjoy it in the spa.

Until Next Time

Vermont has this inviting quality that makes it hard to leave. Its understated charm and beauty paired with its slow-paced lifestyle makes it a destination I can count on when I need to escape for a few days of recharging. I’m so thankful to Phillip for bringing me here two years ago and even more grateful that I got to share it with my mom this fall.

I hope this guide helps you plan your next Vermont getaway. As always, please leave a comment and let me know what you think!

Happy Travels,

Ashley