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Unless you hate snow, any time is the best time to visit New England! Every season has something different to offer. Explore some of the best spots in New England that showcase the charm, history, and unique experiences New England has to offer. Guests share personal travel stories and tips, from Stasha Mills-Healy’s highlights of Mystic Seaport and scenic train rides in Connecticut to Patrina Dixon’s cultural tour in Martha’s Vineyard, MA.
Joe Saul-Sehy talks about the perks of off-season travel in Kennebunkport, Maine while Dawn Barclay dives into New England’s darker history with true crime travel spots. Whether you’re planning a trip or just looking for inspiration, this episode offers fresh, diverse ideas for exploring the region.
Keep reading or listen to the podcast episode here.
Prefer to listen elsewhere? Here’s the exact episode on: Apple or Spotify!
We cover:
Stasha Mills-Healy (0:26 – 7:38)
- 🌄 Mystic & Essex Attractions (2:21 – 5:56): Highlights Mystic Seaport, Aquarium, Essex Steam Train & Riverboat, and scenic Connecticut River views.
- 🍕 Iconic Eats & Itinerary Tips (6:14 – 7:17): Recommends lobster rolls, New Haven pizza, and combining Mystic, Essex, and Mohegan Sun for a well-rounded trip.
- 🏛️ New England Charm & Culture (1:17 – 2:20): Notes Yale, historic house museums, and the state’s Revolutionary War roots.
- I included a snippet from our original episode entitled: 10+ Places to Visit in CT for Your Next Bucket List Trip
Patrina Dixon (8:00 – 11:35)
- 🏖️ Martha’s Vineyard Relaxation (8:32 – 9:04): Shares a calming B&B stay with her husband and the appeal of a peaceful island retreat.
- ✊🏽 African-American Heritage Tour (10:10 – 11:12): Describes the powerful and emotional tour detailing Black history and land reclamation efforts on the island.
- 💬 Personal Reflection (11:12 – 11:35): Discusses the significance of connecting with Black history while traveling.
- I included a snippet from our original episode entitled Planning a Martha’s Vineyard Vacation: Tips for All Budgets
Joe Saul-Sehy (11:36 – 17:06)
- ❄️ Winter Kennebunkport Getaway (11:53 – 13:19): Promotes off-season travel for lower prices, fewer crowds, and a cozy New England vibe.
- 🦞 Gourmet Experiences (13:35 – 15:23): Recounts a top-tier lobster dinner at the White Barn Inn and shopping at local boutiques.
- 🎿 Cold-Weather Fun (15:48 – 16:33): Suggests cross-country skiing at Harris Farm and ending the day with hot chocolate.
Dawn Barclay (18:08 – 29:38)
- 🔪 True Crime in New England (19:15 – 27:39): Tells chilling stories from Connecticut, Maine, Massachusetts, and New Hampshire, including serial killers and arson cases.
- 📚 Travel + Crime Book (28:45 – 29:38): Discusses Vacations Can Be Murder, a guide combining true crime stories with road trip itineraries.
- 🧩 Quirky Historical Crimes (25:15 – 26:32): Highlights infamous scammer Charles Ponzi and the origin of the Ponzi scheme.
Shari Leid – Table for 51 (Approx. 29:40 – End)
- 🍽️ A Journey Through Meals & Meaning: In Table for 51: Lessons Learned from Sharing Meals Across America, Shari Leid—author, speaker, and mindset coach—documents meaningful conversations over meals with people across the U.S., emphasizing connection through diversity.
- 🧭 New England Stops: Includes visits to Cushing, ME, Laconia, NH, Newport, RI, Randolph, VT , and Boston, MA.
- 💬 Human Connection Through Story: Her reflections underscore the magic in listening to others’ lived experiences—spotlighting empathy, common ground, and the beauty of human stories across cultures and states.
What is the best time to visit New England?
The best time to visit New England is based on your preferences and budget. If you enjoy warm weather and outdoor activities, summer is ideal for exploring beaches and charming villages. However, if you prefer cooler temperatures and stunning foliage, consider visiting in the fall for breathtaking autumn colors.
What is New England’s best season?
New England’s best season is widely considered to be fall (autumn) — and for good reason:
🍁 Why Fall Stands Out:
- Foliage: The region is famous for its vibrant fall colors—crimson reds, golden yellows, and fiery oranges—thanks to its mix of maple, oak, and birch trees.
- Crisp Air, Cozy Vibes: Cooler temperatures and low humidity make it perfect for outdoor activities like hiking, apple picking, and visiting pumpkin patches.
- Festivals & Food: Fall brings cider donuts, harvest fairs, Oktoberfests, and Thanksgiving traditions rooted in the region’s colonial history.
- Scenic Drives: Routes through the White Mountains in New Hampshire, the Berkshires in Massachusetts, or Vermont’s Route 100 are iconic road trip destinations.
Other Seasonal Highlights:
- Summer: Perfect for destinations like Cape Cod, the Maine coast, or the lakes of New Hampshire, Martha’s Vineyard is lively and beautiful, although it can be crowded and humid at times.
- Winter: Ski resorts in Vermont and New Hampshire shine, but snowstorms and icy roads can make it a mixed bag unless you’re into winter sports.
- Spring: Offers a refreshing thaw and blooming flowers, but mud season and unpredictable weather make it less of a crowd favorite.
👉 If you’re visiting or planning content around New England, late September to mid-October is peak foliage time — often referred to as the region’s “sweet spot.”
How many days do you need to see New England?
How many days you need to visit New England depends on your travel style and what you want to experience. Here are some must-see spots in New England if you’re starting from a blank slate. Also, here’s a breakdown to help you plan:
⭐️ Quick Answer:
- 5–7 days = Great for hitting highlights across 2–3 states
- 10–14 days = Ideal for a more complete New England road trip, may help to see foliage at it’s peak
- 3–4 days = Enough for a focused getaway (e.g., just Vermont or the Maine coast)
🗺️ If You Have 5–7 Days:
You can experience a mix of culture, coast, and countryside:
- Day 1–2: Boston, MA — Freedom Trail, North End, museums
- Day 3–4: Coastal Maine — Portland or Camden + lighthouses & lobster
- Day 5–6: New Hampshire or Vermont — White Mountains or Green Mountains for hiking, foliage, or covered bridges
- Optional Day 7: Rhode Island stop (Newport mansions or Providence)
🚗 For a Full 10–14 Day Itinerary:
This gives you time to visit all six New England states with some breathing room.
- Massachusetts (Boston, Cape Cod)
- Maine (Portland, Acadia National Park)
- New Hampshire (White Mountains)
- Vermont (Woodstock, Stowe, Route 100)
- Connecticut (Mystic, Litchfield Hills)
- Rhode Island (Newport, Block Island)
Great for:
- Fall foliage road trips
- Summer coastal escapes
- History + small towns + nature lovers
✨ 3–4 Day Long Weekend Ideas:
- Fall in Vermont: Stay in Woodstock or Stowe for foliage and farms
- Maine Coast: Portland + Ogunquit or Acadia
- Boston & Cape Cod: Historic + beachy mix
- Newport, RI: Mansions, cliff walk, sailing
Best time to visit New England for Fall Colors
The best time to visit New England for fall colors is typically late September through mid-October, though the peak timing varies by location and elevation.
Here’s a quick breakdown by region and ideal timing:
🍁 Peak Foliage Timing by Region:
These are just estimates. Keep in mind it can be hard to time when the foliage is at peak when planning.
| Region | Best Time to Visit |
|---|---|
| Northern Vermont & New Hampshire | Late Sept – Early Oct |
| Maine (Inland / Mountains) | Late Sept – Early Oct |
| Central VT & NH, Western MA | Early – Mid October |
| Coastal Maine & Southern New England | Mid – Late October |
| Connecticut / Rhode Island | Mid – Late October |
🔥 Top Leaf-Peeping Spots:
- Kancamagus Highway, NH – Classic scenic drive
- Stowe or Woodstock, VT – Quintessential small towns
- Acadia National Park, ME – Coastal cliffs + color
- Mohawk Trail, MA – Historic byway with vibrant foliage
- Litchfield Hills, CT – Gentle hills and country roads
🌦 Tips:
- Book early – Fall is the most popular travel season in New England
- Weekdays are less crowded
- Weather shifts quickly – Layered clothing is your friend
Would you like a suggested foliage road trip route or local recommendations for a specific state?
The least crowded time to visit New England is typically during the shoulder seasons — times between peak tourist periods when crowds thin out but much of the region’s charm remains:
🕰️ Least Crowded Times to Visit New England:
| Season | When | Why It’s Less Crowded |
|---|---|---|
| Late Spring | Mid-May to early June | Before summer tourists arrive; mild weather, blooming flowers |
| Late Fall | Late October to mid-November | After peak foliage but before winter/ski season kicks in |
| Winter (non-holiday) | January to early March | Outside ski towns, it’s very quiet and budget-friendly |
| Early Spring | Late March to mid-April | Still chilly and sometimes muddy — but very few crowds |
✅ Best Bets for Quiet Exploration:
- Coastal towns like Kennebunkport, Newport, or Cape Ann are peaceful in late spring or late fall.
- Mountain towns (Stowe, North Conway) are quiet between ski and summer seasons.
- Boston & cities are less busy in early spring or after the fall tourist wave.
Would you like help picking a quiet destination based on activities or interests (like hiking, history, food, etc.)?
The cheapest time to visit New England is typically during the off-season and shoulder seasons, when demand for lodging, attractions, and flights is lower.
💰 Budget-Friendly Times to Visit New England:
| Timeframe | Why It’s Cheaper |
|---|---|
| Mid-January to early March | Post-holiday lull (except ski towns); discounts on hotels and flights |
| Late March to mid-May | “Mud season” in the mountains, still chilly along the coast – fewer tourists |
| Late October to mid-November | After peak fall foliage but before winter holidays |
| Early December | Before Christmas season fully kicks in – quiet and inexpensive |
🏷️ Cost-Saving Tips:
- Stay mid-week: Avoid weekend surcharges, especially in popular areas like the Berkshires or coastal Maine.
- Book off-the-beaten-path towns: Prices drop outside of hotspots like Bar Harbor or Boston.
- Use off-season deals: Inns and B&Bs often offer specials in early spring or late fall.
- Public transit: Cities like Boston have reliable public transit, saving on car rentals.
