Travel Guide: Manchester, Vermont

This was my third fall in Manchester, Vermont, and I swear it gets better every year! Mid- to late-October is the best time to go because the leaves are just brilliant – the vibrant shades of yellow, orange and red will blow your mind! I’m rounding up some of the outfits I wore on the trip, but at the bottom of this post you’ll find a full review of our resort and what to do & see in Manchester. 
I wore this outfit for a morning spent in downtown Manchester (the downtown is so cute!!). I don’t think this sweater is meant to be worn as a dress, but it was long on me (I’m 5’3) so it went perfectly with over-the-knee boots!
over-the-knee boots, similar but less expensive HERE & HERE
My friends Jessica (@hapatime) and Nichole (@nicholeciotti) were in Vermont the same time as me – you have to follow them!! They’re the cutest girls. We found the cutest little house just a few yards down from our hotel – just look at those leaves!
my outfit: Express off-shoulder top (sized up to a medium) // Paige jeans (on sale!!) // 
over-the-knee boots, similar but less expensive HERE
What I wore the first night in Manchester – I was actually freezing even in a cardigan and scarf! 
Paige jeans (on sale!!) // over-the-knee boots, similar but less expensive HERE
MAC lipstick in “creme cup”

Lunch at Marsh Tavern is the best! Order the tomato soup & grilled cheese combo (and don’t forget the french fries). 

h&m turtleneck sweater (wearing as a dress) // buffalo check scarf
This was taken in the Equinox Resort’s courtyard – I love the mums they have everywhere! This lavender Free People sweater matched perfectly with the flowers.
  Free People sweater (comes in six different colors!), also love this lavender one // white pants
 over-the-knee boots, similar but less expensive HERE and HERE // Styled Collection coin necklaces
MAC lipstick in “creme cup”

Another shot from downtown Manchester. This scarf is my absolute FAVORITE scarf of all time! It kept me warm the whole time in Vermont, and I wore it on the plane there and back! 

 h&m cable knit sweater (only sold in stores), similar here // Free People scarf
Paige jeans (on sale!) // exact over-the-knee boots, similar but less expensive HERE & HERE
MAC lipstick in “creme cup”

Ok this sweater was also another favorite from my trip – I ended up going back and buying it in the cream color and olive green color when I got home because I loved it so much. I sized up to a medium for a looser, off-shoulder fit.

 Express off-shoulder top (sized up to a medium) // Paige jeans (on sale!!) // over-the-knee boots, similar but less expensive HERE // Styled Collection coin necklaces
One thing you definitely have to do while in Manchester is check out Equinox Pond! Its so beautiful, especially the reflection of the leaves on the pond. 
If you can’t tell from my photos lately, I’m addicted to over-the-knee boots. I can’t stop wearing them! They are perfect for Vermont because they kept my legs warm, too!
fuzzy sweater // skort // exact over-the-knee boots, similar but less expensive HERE & HERE 
Lastly, I am obsesssssed with this tassel poncho! We took Winnie on a walk one morning and this is what I wore for the morning/lunch. 
tassel trim wrap, also like this poncho // white tee (only $25) // Good American jeans
MAC lipstick in “mehr”

*Equinox ResortOne of my favorite hotels in the entire world! The Equinox Resort is located at the bottom of Mount Equinox in Manchester. The hotel is so dreamy and picturesque – picture a large white house with green shutters, lots of flowers and rocking chairs on the porch. The inn itself is historic (several Presidents have stayed there!) and so charming – although it is old, all of the rooms have been updated and are incredibly spacious and well-appointed. Our room had tons of windows (with a great view of the mountains) and super comfy beds. Plus, it’s DOG FRIENDLY! I brought Winnie with me this year, which was particularly special – during last year’s trip to Vermont, I was researching dog breeds the whole time and was so anxious to have a pup of my own! Some other notable features of the inn include a golf course, award-winning spa and a fire pit out back (where we enjoyed dessert and a glass of wine). Plus, it’s just insanely beautiful. You’ll want to bring your camera!
*Marsh Tavern: We ate at Marsh Tavern almost every day! This historic little restaurant located in the Equinox Resort has both indoor and outdoor seating (sit on the patio if the weather is nice!) and delicious food. I loved both the ham sandwich (on pretzel bread) and the grilled cheese and tomato soup combo.
*Gringo Jack’s: Located on Main St. in downtown Manchester, Gringo Jack’s is a Mexican restaurant with amazing atmosphere. I crave Mexican food almost every day, so it was essential that we find a Mexican restaurant, and this one did not disappoint! The guacamole was amazzzzing and so were the cilantro-lime chicken fajitas.
*Up for Breakfast: This local breakfast joint is a favorite – you have to go up a flight of stairs and it’s pretty small inside, but it’s worth it for the great breakfast, from the coffee to the omelets, bread and homemade jam. 
*Ye Olde Tavern: This is a great restaurant for a dinner date – it’s a tavern that’s been around since 1790 and it’s known as having some the best food in town. You can feel the old colonial atmosphere and charm right from the start, and the staff is friendly and professional. The menu consists of many  New England specials, like Yankee Pot Roast, Lobster Bisque and Crispy Duck. 
*Spiral Press Cafe: I LOVE this place because it’s a cafe and bookstore, all in one (did someone say books?! I’m there!). They have really good coffee and sandwiches. 
*Equinox Pond: You have to visit Equinox Pond while you’re in Manchester (especially if you’re there in the fall). Located near the base of Mount Equinox, Equinox Pond and the surrounding land are part of the Equinox Preservation Trust, which was established in 1996 and includes more than 914 acres of protected land. The pond is beautiful and incredibly serene. 
*Skyline Drive: There’s no better way to enjoy the splendor of Vermont and the fall trees than taking a little road trip down Skyline Drive. At 3,848 feet above sea level, the summit offers breathtaking panoramic views of the Green, White, Adirondack, Berkshire and Taconic mountain ranges. Again, bring your camera!! 
*Outlet shops: Surprisingly, there’s a TON of good shopping in this little New England town! There are a ton of outlet shops, including Kate Spade, J.Crew, UGG, Ann Taylor, Armani, Michael Kors and more. You could easily spend a whole day shopping til’ you drop. 
*Lye Brook Falls: The heavily wooded Lye Brook Falls trail runs for 2 miles through the Lye Brook Wilderness near Manchester. Near the southern end of the trail, you’ll find a cascading 125-foot waterfall, one of Vermont’s highest and most impressive.
*Fly into Albany and rent a car: We flew into Albany, NY, and rented a car to drive to Manchester. It’s about an hour and a half drive, but it flies by because its so scenic! The reason you definitely want a car in Manchester is so that you can take day trips to nearby towns and apple orchards, or head up the Skyline Drive to the top of Mount Equinox. 
*Pack warm clothes: Despite what you may think, Manchester starts to get very cool in September (unlike the rest of the country which is still experiencing heat!). It was in the 60s during the day and dropped down into the 40s and 30s at night while we were there. We were worried we didn’t pack warm enough clothes – everyone else was walking around in beanies and had gloves on! If you go during the Winter, you’ll really want to bundle up.

Let me know in the comments if you have any questions!!


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  1. Beautiful photos Cait! This has totally inspired me to travel to Vermont, I've always wanted to go because it looks and sounds like such a magical place – now I definitely have to!

    I hope you're having a lovely Thursday,

  2. It looks like the perfect gateway, love your outfits.


  3. I have that same sweater from H&M (in tan) and thought it was a dress too! Love all of your looks!

    xo, Carey

  4. This makes me want to book a trip there next year! What a cute town and I love how pretty the leaves are!

  5. I was there exactly when you were, it's incredible there. We love the shops there and the Seasons Restaurant is another good spot to eat for lunch.

  6. Oh my goodness.. looks like such a fun time! Love love love all your outfits!! You look amazing!! Esp loving those OTK boots! <3

    Katie |

  7. Such a wonderful post – and your outfits are on point!!


  8. All of your outfits are precious!! I'm dying to visit Vermont in the fall 🙂

  9. That first picture is so dreamy, Caitlin!!! Those stars are unreal. It looks as though you had a wonderful trip. You girls are all so stylish!

    Arum Lilea

  10. Oh how wonderful photos with such a magical vibe on them! 🙂

  11. Ugh, this sounds sooo amazing, Caitlin! I'm definitely filing this away just for the scenic drive part, haha! I love all of your outfits and you're making me want those OTK boots!!!

    She Sweats Diamonds

  12. Love all the outfits!

  13. The place looks gorgeous in your photos! I love the outfits and now I want to visit there so bad. I haven't been to vermont since I was a baby!

    Kim .. the best long cardis and giveaway!

  14. What an amazing trip! I love all your cozy looks too! They were all so perfect for the mini vaca!

  15. This looks like such a beautiful city! Thanks for all of the travel tips.

    xx, Tomi

  16. This place looks so beautiful! And I had no idea you were 5'3! I learn something new every time I come here

  17. Your makeup is flawless! Manchester makes me think of the UK city but these looks beautiful. I love your knitwear!

    T x