Newport RI in the Fall + Connecticut Road Trip | 7-Day New England Itinerary

Looking for how to spend 7 days in the fall up on the East Coast? We spent 7 days in New England in October and I'm sharing the full itinerary: where we stayed, where we ate, things to do in Newport RI and Essex CT, and the little shops we can't stop talking about. Newport RI in the fall, plus a cozy Connecticut road trip should be your next travel bucket list travel item. Save this one for your next New England road trip 🍂 I went for my bachelorette to Newport, Rhode Island during October specifically I could watch the fall foliage with my besties, enjoy some fall weather, and attend the Bowen's Wharf Seafood Festival. Everyone flew home Sunday, and my Mom rented a car and came up and met me, and we had a mother daughter trip for the next few days exploring Connecticut and some more of Rhode Island. This made for the ultimate cozy girls trip AND mom/daughter trip, so if you're in need of an itinerary- just copy mine! 🍂 7-DAY NEW ENGLAND ITINERARY 🍂 THURSDAY | Fly into PVD Stay: Sailor's Den, Newport Order pizza from Mother's Pizzeria Walk around town and get the lay of the land Pick up wine at Downtown Liquors, catch up, and people watch Grab ice cream at Get the Scoop FRIDAY | Newport RI, Day 1 Coffee and breakfast at The Nitro Bar Explore the neighborhood - stop into Charter Books! Walk to your Mansion tour at The Breakers through the famous Cliff Walk Stop into Buskers Pub & Restaurant (we tried their pumpkin martinis!) Dinner at Pasta Beach SATURDAY | Newport RI, Day 2 Breakfast at Co-Dough (and maybe The Nitro Bar.. again. lol) Shopping and antiques - we loved VS Vintage and Leeside Antiques If you go when we went- enjoy the Newport Seafood Festival!! If not, explore the marina and pick up a lobster roll Newport Lobster Shack Debrief at Dueling Pianos and grab a drink and a snack Happy hour + sunset at Castle Hill Inn Dueling pianos for a drink Wanna go out? Hit up Fastnet Pub Would rather get a sweet treat? Walk to Cupcake Charlie's I picked up a few souvenirs throughout the weekend at the General Store and the Life is Good Newport. If you want some food alternatives, The Hungry Monkey is good, or there was always a line for the Corner Cafe. SUNDAY | Newport RI, Day 3 (Yes I went to The Nitro Bar and Co-Dough again. Cinnamonrollmaxxing with the cinnamon roll AND cinnamon roll float latte from them.) Seafood Festival part 2!! Eat as much as possible from all the vendors at the Bowen's Wharf Seafood Festival Check in at Carriage House Inn (take a nap... hahaha) Collins Beach for sunset Dinner at Bar 'Cino MONDAY | Rhode Island to Connecticut Check in at Niantic Inn Things to do in Essex CT: Gracie's Corner, Chocolate Geeks (get the cookie!), Essex Park, the lighthouse off Pratt St., and Goods & Curiosities The Cheese Shop in Centerbrook Niantic: Anna Pearl's Curiosities (a lot of other stores were closed, so check hours before you go!) Hole in the Wall Beach + the boardwalk for sunset Dinner at 374 Kitchen & Cocktails Chocolate soft serve at Gumdrops & Lollipops (cash only!) TUESDAY | Old Saybrook, Chester + Black Point Sift Bakery on the way to Old Saybrook Essex Saybrook Antique Village (say hi to Judy for us!) Apple picking in Connecticut at Scott's CT Valley Orchards Chester Sunday Market (FIRE sandwiches) Drive to Gillette Castle (we skipped the ferry because of timing) Sunset and house-watching at the tip of Black Point (just drive around! It's all so cute) Casual dinner at Skippers (for a final lobster roll + lobster bisque) WEDNESDAY | Wickford RI + fly home Sandwich at Shayna's Place Last minute souvenir shopping at Shop My Paris Maison, The Impressed Olive, the chocolate shoppe, Different Drummer, and Seacoast Sweets (SO many cute shops here in Wickford!) Quick pit stop at Seven Stars Bakery on the way to PVD for your airport snack 🍩 DIDN'T MAKE IT, BUT WISH WE HAD Flanders Donut (maple bacon) Beach Donuts (their apple cider donut) Connecticut College Arboretum Honestly, the best part was the random stops, like Hamburg Cove Yacht Club and Sunset Pond in Essex. Some of the best small towns in Connecticut are the ones you just pull over for. I hope you enjoy the sights and make this trip to see it for yourself! 0:00 Intro 0:10 Thursday: Fly into Providence 0:26 Friday: Newport RI Day 1 + The Breakers 0:58 Saturday: Newport Seafood Festival 1:36 Sunday: Newport Weekend + Collins Beach 2:00 Monday: Essex CT + Niantic 2:32 Tuesday: Chester CT, Gillette Castle + Black Point 3:02 Wednesday: Wickford RI + fly home ✨ When I'm not traveling, I'm co-running Mad Banana marketing, where we build websites and do SEO for small businesses so the right people can actually find you online. Come say hi: https://madbananamktg.com #NewportRI #NewEnglandFall #NewEnglandRoadTrip #EssexCT #FallTravel #TravelVlog