Will and I are heading to Vermont this weekend and I’ve been researching non-stop. I haven’t been to Vermont since a family ski trip there probably fifteen years ago and my Texan husband has never been so we’re both looking forward to exploring and hopefully spotting some early fall foliage (fingers crossed!). We’re staying at the Woodstock Inn and know we want to eat at the Simon Pearce restaurant (where you can also watch them blow glass in person — I definitely want to pick up a souvenir or two for our house!). Besides that I’ve bookmarked a bunch of picturesque little towns, covered bridges, and restaurants but I’d LOVE your two cents if you have any must-see favorites in the Green Mountain state. As of now we’re planning on taking a scenic route through Manchester on our way north and road tripping to Waitsfield and Warren at some point before our drive home but again I’m all ears!

It’s going to be around 60-65 degrees during our visit and I’m so excited to embrace sweater weather in full force. I recently added this twist-front style to my closet and it’s so cute with high-waisted jeans… I wish I’d had a dark wash pair like these to style it with for these photos so those may be my next purchase. I’m also tempted to try it backwards with the crewneck in the front and the v-neck and twist in the back but I wore it the “right” way so you could see this pretty little disc necklace from the Moon & Meadow collection at Bloomingdale’s (so many pretty and timeless pieces — I love this and this). And I’ve been living in these Tretorn sneakers — they’re true to size and seriously feel like walking on a cloud.

sage the label hold you close twist-front sweater and tretorn women's nylite plus lace up sneakers in white and green

sage the label hold you close twist-front sweater

sage the label hold you close twist-front sweater and moon & meadow 14k yellow gold disc pendant necklace

sage the label hold you close twist-front sweater and tretorn nylite plus sneakers in green and white

sage the label hold you close twist-front sweater and moon & meadow 14k yellow gold disc pendant necklace on design darling

sage the label hold you close twist-front sweater with moon & meadow 14k yellow gold disc pendant necklace

design darling tretorn sneakers

Sage the Label twist-front sweater (also love this, this, and this)  //  Moon & Meadow necklace

Ray-Ban clubmasters  //  J.Crew jeans (similar)  //  Tretorn sneakers

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*This post is sponsored by Bloomingdale’s. Thank you for supporting the brands that support Design Darling!


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  1. I got married up in Vermont earlier this summer and have spent a lot of time in Warren/Waitsfield/Stowe! In addition to Simon Pearce, I would definitely eat at Worthy Kitchen – truly delicious and they have a fantastic VT craft beer menu.

    In Warren; a visit to the Warren Store is a must. If you want a fairly short hike, drive up Lincoln Gap (steepest paved mile in America!) and hike Sunset Ridge for a pretty Vista at the end.

    Peasant on the Waitsfield covered bridge is also a great restaurant option in town. The gas station across the street (and the previously mentioned Warren Store) are usually good places to pick up some VT beer – Heady Topper or Lawson’s

  2. You MUST go to Manchester Vermont! I go on a girls trip their every year and it is amazing!!! You have to go to the Ye Ole Tavern, they have the most delicious food and the building is filled with history!! I love love love Manchester Vermont. Then if you are there for breakfast you must go to Up for Breakfast which is a tiny breakfast spot in Manchester-square which usually always has a wait but is so worth it. I’m headed there in November and I am so excited!! I hope you enjoy Vermont it is so beautiful!
    Xo, Kelsey

  3. My boyfriend and I spend a lot of time in Vermont and are taking our first trip to Manchester/ Dorset in 2 weeks! After years of ski houses I can tell you not to miss the Woodstock Farmers Market in Woodstock, Mad Taco in Warren (seriously the most amazing tacos you will ever have), a drink at Tracks at the Pitcher Inn, and a visit to the Warren Store across the street.

    Its technically not my recommendation yet, but I have planned a serious visit to In Stitches – the needlepoint store in Dorset. Several well known modern needlepoint designers are from Dorset and apparently, they have an incredible collection of canvases.

    Lastly, whatever you do – don’t leave the state without buying a jar of Fox Hollow Mustard. It’s balsamic and garlic spicy mustard and it will make anything you eat so, so much more delicious!

  4. The Hildene Reaidence in manchester is a beautiful property with an interesting history (the Lincoln family) and a restored Pullman Car! It will be beautiful in that weather and the staff is lovely. Definitely a must see!

  5. I went to Dartmouth and would echo what other readers have said about the area being worth a trip (about half an hour from Woodstock. Four Aces is the classic New England diner, complete with holly decor and a magic 8 ball on each table. The popovers and maple butter are to die for. The King Arthur Flour HQ has a cafe with delicious baked goods (try the sticky bun!), a huge baking store with hard to find items, and amazing cooking classes. Pine has great cocktails and food, and the view of the green in the fall is gorgeous. Canoe Club is a great place to go for a glass of wine and speakers, live music, etc.

    Woodstock has an amazing vintage store full of 1950s plaid skirts and letterman jackets, 40s costume jewelry, and 30s furs. It’s so fun to browse even if you don’t buy anything. Mon Vert is cant miss for coffee, brunch, and instagrammable wallpaper. Cloudland farm is to die for, but make reservations early.

    Can’t wait to hear about the trip. Living vicariously through you!

  6. definitely stroll through Hanover! Pine is delicious for any meal, or just for a cocktail. Dirt Cowboy coffee is incredible. and Dartmouth is super cute 🙂 In Queechee, go to the Cabot Cheese store and see the Gorge!!

  7. So many great recommendations already! I went to Dartmouth and am biased, but would totally recommend hopping over the river to Hanover to check out the campus and stroll through Main St in Hanover. Drinks on the Pine patio while overlooking the Green! King Arthur Flour in Norwich is worth stopping at to pick up some culinary gifts and maybe take a baking class!

  8. Also, Dog Mountain was amazing. It is the gallery for Stephen Huneck and also a large dog park with a chapel honoring dogs that have passed away.

  9. The Woodstock Farmers Market is super cute and we also loved Chef Brad’s Crazy Side in Queechee. I would also highly recommend visiting the Harpoon Brewery and Silo Distillery which were fairly close to Woodstock.

  10. My family has had a house in Manchester for the past 30+ years— it’s the cutest little town! Definitely agree to pop into the Northshire book store to stock up on a good read for the drive. The Equinox is a gorgeous hotel- you can grab lunch at The Marsh Tavern or take a glass of wine out by the fire pit. Also consider driving up to Equinox Pond for gorgeous views of the foliage. Lately, take a spin through the Orvis flagship store- you’ll love it!

  11. Just visited Vermont for the first time last week with my mom for a long weekend, and we had the best time! We were staying in Manchester, which was so lovely, but took a couple drives to visit Woodstock and Queechee as well. Woodstock is just so cute! We visited Simon Pearce and had the most wonderful dinner at the restaurant there. I’d also second a visit to the Vermont Country Store for fudge and cheese samples! Have a wonderful trip!

  12. The town of Middlebury, home to Middlebury College, is wonderful. Check out Costello’s Italian market, which is such an unexpected gem. The Lake Champlain region and Burlington are also amazing. Can’t go wrong in Vermont!

  13. My favorite state! Well, tied with Maine 🙂

    Your trip plans sound amazing! Be sure to allow just a little time to experience the spa at the Woodstock Inn – even if you don’t opt for a full-treatment, you can do a day pass and enjoy the sauna/steam/hot tub/etc. Best part of staying there!

    Simon Pearce is a great restaurant! And you’ll love the Farmhouse Pottery shop. It’s a drive, but the last time we stayed in Woodstock, we drove to Ludlow for a meal at the Downtown Grocery. If you happen to drive through South Londonderry, our favorite VT meal was at SoLo Farm & Table.

    Seconding the recommendations for Warren and the Pitcher Inn, even if just for a meal. You’ll want to head back for a proper weekend long stay at the Pitcher Inn if you see it. The best people there!

    The hiking in Woodstock is great – our favorite is the short walk up Mt. Tom!

    Here is the VT tag on our site –

    Have fun!!

  14. I went to Woodstock last year – SO CUTE! Maybe 20 minutes outside the town there is an alpaca farm, Living the Dream Alpaca Farm, and you can feed them and they were too cute. Next door is a Cabot Cheese store where you can literally try every cheese ever and buy anything Cabot you could ever want.

    Report back on Manchester, I am going in November (even just the views!)

    have a great time!

  15. I live in Waitsfield, it’s beautiful here right now and all the leaves are starting to change! If you come to Waitsfield: The Sweet Spot for lunch or an iced coffee and a treat. The farmer’s market is Saturday 9-1 and has a ton of amazing vendors. The Taste Place for a cheese board, local cider, beer, and wine; sit by the fireplace, so cozy. You can also take a walk on any of the Mad River Paths, you can look it up online, there are several around town and all have great spots by the Mad River for photos. American Flatbread for dinner!!

    Definitely Warren Falls if you want to take a dip in the river or just for a gorgeous spot for a picnic. You can get sandwiches and local cider/beer at the Warren Store or the Warren Community Market and go to Warren Falls. There’s a parking lot and it’s right on Rt 100.

    Have so much fun!!

  16. Mt Tom is a cute easy hike just outside of Woodstock. Beautiful views over town. The whole thing is 4-5 miles, but you can do a shorter walk just to the top (skip the lake) to get the views. Park at Billings Farm. Brattleboro is probably on your way from CT – The Whetstone Station Restaurant and Brewery is right on the river and has gorgeous views out over the water.

  17. Simon Pearce is the best!

    Drinks and dinner at Pine in Hanover. A beer/drink at the porch of the Norwich Inn, or at Carpenter and Main. Hike Moosilauke. Dinner at Worthy Burger. The Billings Museum. I spent 8 years there, it’s the best place ever!

  18. Have fun! We usually ski every winter at Sugarbush, which is near the towns of Warren and Waitsfield. My favorite spots to eat are Peasant, Pitcher Inn (they have a fancier restaurant upstairs, and a tavern downstairs that is super cozy in the winter with a fireplace and woodsy decor), and Hyde Away Inn (more casual). I’ve only been during ski season but fall should be beautiful!!

  19. Just recently visited Dartmouth and hopped over the state line to VT to go to Worthy Kitchen, it was amazing! Would highly recommend – farm to table, delicious and has a rotating menu. Hope you get a chance to check it out!

  20. My husband and I did a roadtrip thru New England a couple summers ago and The Woodstock Inn was hands down, our favorite place to stay. Simon Pearce is the most beautiful. Walking around to see the covered bridges is fun. I wanted to go to Long Trail, but we were too lazy – next time! Enjoy the weekend – I hope you have gorgeous weather.

  21. Eat dinner at Cloudland Farm. Literal farm-to-table meal, they change the menu weekly (a 3-course set meal) and it’s only open for dinner on thursday, friday and saturday. It’s incredible!! Also, it is BYOB. Highly recommend. Loved it so much we did our rehearsal dinner there!

    Worthy Kitchen for incredible burgers:

    Enjoy time at the Woodstock Inn Spa.

    Pick up sandwiches at the Woodstock Farmer’s Market (amazing deli) and go for a hike up Mt. Tom. Also pick up the maple shortbread cookies from vt moonlight cookies, they’re addictive.

    Also love Simon Pearce- the restaurant is fabulous and so fun to watch the glassblowing. Upstairs they have their “outlet”- basically pieces that have a slight imperfection that are seriously discounted (ex: beautiful vase for $40). And check out the Queechee Gorge.

  22. You definitely need to make a stop at the Dorset Inn! It’s just up the road from Manchester Center and is the perfect “New England” Inn. Along the same road are The Kitchen Store at JK Adams and a cafe called Dorset Rising, both wonderful as well. Have fun!!

  23. You definitely need to stop at the Dorset Inn! Its just up the road from Manchester Center. It’s absolutely lovely and the perfect “New England” Inn. Along the same road is the Kitchen Store at JK Adams and Dorset Rising, which are both great as well. Have fun!!

  24. Check out Quechee Gorge, it’s called “Vermont’s Little Grand Canyon” and is really very beautiful! You can hike or just enjoy a few walking trails there. Or if you wanted to go a little farther north beyond Waitsfield/Warren you could check out Cold Hollow Cider Mill in Waterbury. They make apple cider (and really delicious cider slushies), a gift shop, have hard cider tastings, and Boyden Valley Winery has a tasting room there too. The South Woodstock County Store is always a cute place to stop for a quick bite and Farmhouse Pottery never disappoints!

    Love VT and hope you enjoy your time there!

  25. Northshire Books in Manchester. Walk the Queechee Gorge while there for Simon Pearce. The Shelbunrne Museum is a must must must visit. And best of all the Inn at Shelburne Farms for a meal. Visit the farm too… wander the entire property! And book a room for next time! Burlington…wonderful city.

  26. Not in VT but the Barbour Clearance Center is in NH…it is a gold mine! When I went, they had 50% off everything (and the items are exactly the same as you’d get in-store, they’re just overstock from retailers) but they said it’s usually a minimum of 30% off. It’s worth the detour if you’re not pressed for time 🙂 (oh, and they said you could call and ask what the discount is before you go…they just don’t post online!)

  27. Definitely think about going to the Norwich Farmer’s Market if you are in the area early Sat morning ( and perhaps to King Arthur Flour nearby to pick up gifts for the bakers in your life. Hanover NH is just over the bridge from Norwich- home of Dartmouth College- and it is always fun to walk around Occum Pond and walk around the campus. All are a short drive from Woodstock.

    1. The Apple Barn in Bennington for cider doughnuts, the Orvis Store in Manchester to pick up a toy for Rory, the Vermont Country Store in Weston for cheese and fudge samples and penny candy, you’ll drive past Long Trail Brewery but Harpoon is right next to Simon Pearce!